Cyclopentylamine → HCID 11374476, compound

HRID 1825837Notes

Reaction equation

HRID 1825837 reaction equation
O=[CH:2][CH2:3][N:4]1[CH:12]=[C:11]2[C:6]([CH:7]=[C:8]([NH:13][C:14]([NH:16][C:17]3[CH:22]=[CH:21][C:20]([O:23][C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=4)=[CH:19][CH:18]=3)=[O:15])[CH:9]=[CH:10]2)=[N:5]1.[CH:30]1([NH2:35])[CH2:34][CH2:33][CH2:32][CH2:31]1.C([BH3-])#N.[Na+]>C1COCC1.C(OCC)(=O)C>[CH:30]1([NH:35][CH2:2][CH2:3][N:4]2[CH:12]=[C:11]3[C:6]([CH:7]=[C:8]([NH:13][C:14]([NH:16][C:17]4[CH:22]=[CH:21][C:20]([O:23][C:24]5[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=5)=[CH:19][CH:18]=4)=[O:15])[CH:9]=[CH:10]3)=[N:5]2)[CH2:34][CH2:33][CH2:32][CH2:31]1

Participants

6

Reactant 3

HCID 2906CyclopentylamineHCID 5003444Sodium cyanoborohydrideHCID 22138906HCID 22138906, compound

Product 1

HCID 11374476HCID 11374476, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 1-[2-(2-oxo-ethyl)-2H-indazol-6-yl]-3-(4-phenoxy-phenyl)urea (20 mg, 0.05 mmol) and cyclopentylamine (10 mL, 0.10 mmol) in THF (0.5 mL) was shaken at room temperature for 30 minutes. 1M Sodium cyanoborohydride in THF (104 μL, 0.10 mmol) was added and the solution was shaken at room temperature for 16 hours. The sample was diluted with ethyl acetate, washed with water, concentrated under reduced pressure and purified by RP-HPLC. 1H NMR (300 MHz, DMSO-d6) δ ppm 1.6 (m, 6 H), 2.0 (m, 2 H), 3.55 (m, 2 H), 4.35 (m, 2 H), 4.70 (t, 2 H), 6.97 (m, 5 H), 7.12 (m, 1 H), 7.35 (m, 2 H), 7.52 (m, 2 H), 7.65 (d, 1 H), 7.95 (s, 1 H), 8.35 (s, 1 H) and 8.70 (m, 2 H.); MS (ESI) 456 (M+H)+.

Workup

  1. stirringthe solution was shaken at room temperature for 16 hours
  2. washwashed with water
  3. concentrationconcentrated under reduced pressure
  4. custompurified by RP-HPLC

Sources & evidence

ORD record
ord-d7bb1e08bf9d4bf987ba227489f8f65a
Source dataset
uspto-grants-2006_05
Patent number
US07049307B2

Reaction notes

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