Methanol → HCID 178491832, compound

HRID 2095642Notes

Reaction equation

HRID 2095642 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[CH:23]=[N:24][N:25]([C@H:28]4[CH2:33][CH2:32][C@H:31]([C:34]([O:36]CC)=[O:35])[CH2:30][CH2:29]4)[C:26]=3[CH3:27])[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[CH:23]=[N:24][N:25]([C@H:28]4[CH2:33][CH2:32][C@H:31]([C:34]([OH:36])=[O:35])[CH2:30][CH2:29]4)[C:26]=3[CH3:27])[CH:20]=2)[NH:15][CH:14]=1)[CH3:12]

Participants

5

Reactant 4

HCID 887MethanolHCID 962WaterHCID 3939Lithium HydroxideHCID 178472397HCID 178472397, compound

Product 1

HCID 178491832HCID 178491832, compound

Procedure

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}-5-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=511.19/513.19 (100/50) [MH+]. HPLC: tR=1.44 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-09dddfbe5fa047d49d48a6b8d6e87c04
Source dataset
uspto-grants-2013_05
Patent number
US08445510B2

Reaction notes

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