Methanol → HCID 67518126, compound

HRID 1465702Notes

Reaction equation

HRID 1465702 reaction equation
Cl[CH2:2][C:3]([N:5]1[CH2:10][CH2:9][CH2:8][CH2:7][CH2:6]1)=[O:4].N1CCCC([N:17]2[CH:21]=[N:20][C:19]([C:22]3[CH:23]=[C:24]4[C:28](=[CH:29][CH:30]=3)[NH:27][N:26]=[C:25]4[C:31]3[CH:36]=[CH:35][N:34]=[CH:33][CH:32]=3)=[N:18]2)C1.C([N:39]([CH2:42][CH3:43])[CH2:40][CH3:41])C.[CH3:44]O>>[N:5]1([C:3](=[O:4])[CH2:2][N:39]2[CH2:40][CH2:41][CH2:44][C@@H:43]([C:21]3[NH:17][N:18]=[C:19]([C:22]4[CH:23]=[C:24]5[C:28](=[CH:29][CH:30]=4)[NH:27][N:26]=[C:25]5[C:31]4[CH:36]=[CH:35][N:34]=[CH:33][CH:32]=4)[N:20]=3)[CH2:42]2)[CH2:10][CH2:9][CH2:8][CH2:7][CH2:6]1

Participants

5

Reactant 4

HCID 887MethanolHCID 8471TriethylamineHCID 2223122-Chloro-1-piperidine-1-yl-ethanoneHCID 86695580HCID 86695580, compound

Product 1

HCID 67518126HCID 67518126, compound

Conditions

Temperature
50 °C

Procedure

Added 2-chloro-1-(piperidin-1-yl)ethanone (50 mg, 0.31 mmol) to a solution of (R)-5-(5-(-(piperidin-3-yl)-1H-1,2,4-triazol-3-yl)-3-(pyridin-4-yl)-1H-indazole (47 mg, 0.106 mmol) and triethylamine (0.3 ml, 2.1 mmol) in MeOH (10 ml). After stirred at 50° C. overnight, reaction mixture was concentrated then purified on preparative TLC (20×20 cm) eluting with 10% v/v MeOH/MeCl2 saturated with NH4OH to yield (R)-1-(piperidin-1-yl)-2-(3-(3-(3-(pyridin-4-yl)-1H-indazol-5-yl)-1H-1,2,4-triazol-5-yl)piperidin-1-yl)ethanone as a white solid (23 mg).

Workup

  1. customreaction mixture
  2. concentrationwas concentrated
  3. customthen purified on preparative TLC (20×20 cm)
  4. washeluting with 10% v/v MeOH/MeCl2 saturated with NH4OH

Sources & evidence

ORD record
ord-0be17eecfcc94316902498b988dd9372
Source dataset
uspto-grants-2015_04
Patent number
US08999966B2

Reaction notes

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