3-amino-3-cyclopropylpropan-1-ol

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: This compound was prepared from ethyl 7-[(4-fluorophenyl)methyl]-4-hydroxy-2-oxo-1-[2-(2-oxo-1-piperidinyl)ethyl]-1,2-dihydro-1,5-naphthyridine-3-carboxylate and 3-amino-3-cyclopropyl-1-propanol using methods similar to Example 563 to provide an off-white solid: 1H NMR (300 MHz, DMSO-d6) δ ppm 0.24-0.34 (m, 2 H), 0.38-0.46 (m, 1 H), 0.52 (t, J=8.74 Hz, 1 H), 1.00-1.11 (m, 1 H), 1.54-1.67 (m, 4 H), 1.75-1.88 (m, 2 H), 2.04 (s, 2 H), 3.28 (t, J=5.69 Hz, 3 H), 3.46-3.60 (m, 5 H), 4.17 (s, 2 H), 4.41 (t, J=6.95 Hz, 2 H), 7.11-7.17 (m, 2 H), 7.38-7.45 (m, 2 H), 8.22 (s, 1 H), 8.56 (d, J=1.47 Hz, 1 H), 10.36 (d, J=8.63 Hz, 1 H), 17.23 (s, 1 H); ES+ MS: 537 (M+H+). to provide an off-white solid

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: The title compound was prepared using 5-cyano-1-(3-trifluoromethoxybenzyl)-1H-indole-2-carboxylic acid [prepared from 3-(trifluoromethoxy)benzyl bromide and ethyl 5-cyanoindole-2-carboxylate] and 3-amino-3-cyclopropylpropan-1-ol in a manner similar to that described in Example 11.

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: The title compound was prepared using 5-cyano-1-(3-trifluoromethoxybenzyl)-1H-indole-2-carboxylic acid [prepared from 3-(trifluoromethoxy)benzyl bromide and ethyl 5-cyanoindole-2-carboxylate] and 3-amino-3-cyclopropylpropan-1-ol in a manner similar to that described in Example 11.

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: 3-Amino-3-cyclopropylpropan-1-ol (30 mg, 0.26 mmol) was added to a solution of 1-tert-butyl 4-methyl 3-formyl-1H-pyrrolo[2,3-b]pyridine-1,4-dicarboxylate (39.6 mg, 0.13 mmol) in MeOH (3 mL) with AcOH (2 drops). After stirring for 90 min at rt, sodium cyanoborohydride (33 mg, 0.53 mmol) was added, and the reaction was stirred for an additional 3 h. The mixture was quenched with sat. NaHCO3 solution and extracted with ethyl acetate. The organics were dried over MgSO4 and concentrated in vacuo to give 50 mg of crude 1-tert-butyl 4-methyl 3-((1-cyclopropyl-3-hydroxypropylamino)methyl)-1H-pyrrolo[2,3-b]pyridine-1,4-dicarboxylate as a yellow oil which was used without further purification. [M+H] found 404. the reaction was stirred for an additional 3 h The mixture was quenched with sat. NaHCO3 solution extracted with ethyl acetate The organics were dried over MgSO4 concentrated in vacuo

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: The title compound was synthesized in analogy to Example 12d, using 5-chloro-4-cyclopropylmethoxy-pyridine-2-carboxylic acid and γ-amino-cyclopropanepropanol (CAN 683220-79-3) as starting materials and isolated (27 mg, 83%) as colorless oil; LC-MS (UV peak area, m/z) 97.6%, 325.1313 (MH+). isolated (27 mg, 83%) as colorless oil