Methanol → HCID 178491826, compound

HRID 2095650Notes

Reaction equation

HRID 2095650 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]([CH3:39])=[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[C:23]([CH3:39])=[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 178472400HCID 178472400, compound

Product 1

HCID 178491826HCID 178491826, 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}-3,5-dimethyl-1H-pyrazol-1-yl)cyclohexanecarboxylate (9.00 mg, 0.0163 mmol) in MeOH (1 mL, 30 mmol) was added lithium hydroxide (1.95 mg, 0.0814 mmol) and H2O (0.4 mL, 20 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 at pH 2. The organic layer was concentrated in vacuo to afford the title compound as a white solid. MS (ES+): m/z=525.21/527.21 (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 at pH 2
  3. concentrationThe organic layer was concentrated in vacuo

Sources & evidence

ORD record
ord-70c2fcf4758941899aa191050bf3f82b
Source dataset
uspto-grants-2013_05
Patent number
US08445510B2

Reaction notes

Loading…