Cyclopentylamine → N-{1-[2-(cyclopentylamino)ethyl]-1H-indazol-6-yl}-2-(4-phenoxyphenyl)acetamide

HRID 1790147Notes

Reaction equation

HRID 1790147 reaction equation
O=[CH:2][CH2:3][N:4]1[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([NH:13][C:14](=[O:29])[CH2:15][C:16]3[CH:21]=[CH:20][C:19]([O:22][C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=4)=[CH:18][CH:17]=3)[CH:11]=2)[CH:6]=[N:5]1.[CH:30]1([NH2:35])[CH2:34][CH2:33][CH2:32][CH2:31]1.[BH3-]C#N.[Na+]>C1COCC1.C(OCC)(=O)C>[CH:30]1([NH:35][CH2:2][CH2:3][N:4]2[C:12]3[C:7](=[CH:8][CH:9]=[C:10]([NH:13][C:14](=[O:29])[CH2:15][C:16]4[CH:17]=[CH:18][C:19]([O:22][C:23]5[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=5)=[CH:20][CH:21]=4)[CH:11]=3)[CH:6]=[N:5]2)[CH2:34][CH2:33][CH2:32][CH2:31]1

Participants

6

Reactant 3

HCID 2906CyclopentylamineHCID 5003444Sodium cyanoborohydrideHCID 22036616N-[1-(2-oxoethyl)-1H-indazol-6-yl]-2-(4-phenoxyphenyl)acetamide

Product 1

HCID 11751409N-{1-[2-(cyclopentylamino)ethyl]-1H-indazol-6-yl}-2-(4-phenoxyphenyl)acetamide

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of N-[1-(2-oxoethyl)-1H-indazol-6-yl]-2-(4-phenoxyphenyl)acetamide (20 mg, 0.05 mmol) and cyclopentylamine (10 μL, 0.10 mmol) in THF (1 mL) was stirred at room temperature for 0.5 hours after which NaCNBH3 (0.104 mL, 0.010 mmol, 1 M in THF) was added and the mixture was stirred for an additional 18 hours. The mixture was diluted with ethyl acetate (2 mL), washed with H2O (1 mL), concentrated under reduced pressure and purified by reverse phase-HPLC to provide the title compound. 1H NMR (300 MHz, DMSO-d6) δ ppm 1.5 (m, 6 H), 1.9 (m, 2 H), 2.9 (m, 1 H), 3.4 (m, 2 H), 3.8 (m, 2 H), 4.6 (t, 2 H), 7.0 (m, 4 H), 7.1 (m, 2 H), 7.4 (m, 4 H), 7.7 (m, 1 H), 8.05 (s, 1 H), 8.3 (s, 1 H), 8.6 (m, 1 H), and 10.4 (s, 1 H); MS (ESI) 455.2 (M+H)+.

Workup

  1. additionwas added
  2. washwashed with H2O (1 mL)
  3. concentrationconcentrated under reduced pressure
  4. custompurified by reverse phase-HPLC

Sources & evidence

ORD record
ord-5a48f10fdd91405e9f7c6f0d95002581
Source dataset
uspto-grants-2006_07
Patent number
US07071182B2

Reaction notes

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