Methanol → HCID 178491828, compound

HRID 2095647Notes

Reaction equation

HRID 2095647 reaction equation
[Cl:1][C:2]1[C:7]([F:8])=[CH:6][CH:5]=[C:4]([O:9][CH3:10])[C:3]=1[C@H:11]([C:13]1[C:21]2[C:16](=[N:17][CH:18]=[C:19]([C:22]3[C:23]([CH3:38])=[N:24][N:25]([C@H:27]4[CH2:32][CH2:31][C@H:30]([C:33]([O:35]CC)=[O:34])[CH2:29][CH2:28]4)[CH:26]=3)[CH:20]=2)[NH:15][CH:14]=1)[CH3:12].CO.[OH-].[Li+].O>>[Cl:1][C:2]1[C:7]([F:8])=[CH:6][CH:5]=[C:4]([O:9][CH3:10])[C:3]=1[C@H:11]([C:13]1[C:21]2[C:16](=[N:17][CH:18]=[C:19]([C:22]3[C:23]([CH3:38])=[N:24][N:25]([C@H:27]4[CH2:32][CH2:31][C@H:30]([C:33]([OH:35])=[O:34])[CH2:29][CH2:28]4)[CH:26]=3)[CH:20]=2)[NH:15][CH:14]=1)[CH3:12]

Participants

5

Reactant 4

HCID 887MethanolHCID 962WaterHCID 3939Lithium HydroxideHCID 178472382HCID 178472382, compound

Product 1

HCID 178491828HCID 178491828, compound

Procedure

To a solution of ethyl trans-4-(4-{3-[(1S)-1-(2-chloro-3-fluoro-6-methoxyphenyl)ethyl]-1H-pyrrolo[2,3-b]pyridin-5-yl}-3-methyl-1H-pyrazol-1-yl)cyclohexanecarboxylate (20.0 mg, 0.0371 mmol) in MeOH (3 mL, 70 mmol) was added lithium hydroxide (4.44 mg, 0.186 mmol) and H2O (1 mL, 60 mmol). The mixture was stirred at rt for 2 h. The organic solvent was removed in vacuo, and the material was extracted with DCM and water (pH=2). The organic layer was concentrated in vacuo to afford the title compound as a white solid. MS (ES+): m/z=511.20/513.20 (100/50) [MH+]. HPLC: tR=1.45 min (polar—3 min, UPLC-ACQUITY).

Workup

  1. customThe organic solvent was removed in vacuo
  2. extractionthe material was extracted with DCM and water (pH=2)
  3. concentrationThe organic layer was concentrated in vacuo

Sources & evidence

ORD record
ord-9e3867e7325b46c0ab8f2b71a673dea7
Source dataset
uspto-grants-2013_05
Patent number
US08445510B2

Reaction notes

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