Potassium Hydroxide → HCID 89750984, compound

HRID 1842612Notes

Reaction equation

HRID 1842612 reaction equation
[C:1]([O:5][C:6](=[O:36])[NH:7][C@@H:8]1[CH2:13][CH2:12][CH2:11][C:10]([F:15])([F:14])[C@@H:9]1[NH:16][C:17]([C:19]1[S:20][C:21]([CH2:34][CH3:35])=[C:22]([C:24]2[CH:25]=[N:26][N:27]3[CH:32]=[C:31](Br)[CH:30]=[N:29][C:28]=23)[CH:23]=1)=[O:18])([CH3:4])([CH3:3])[CH3:2].[OH-:37].[K+]>CO>[C:1]([O:5][C:6](=[O:36])[NH:7][C@@H:8]1[CH2:13][CH2:12][CH2:11][C:10]([F:15])([F:14])[C@@H:9]1[NH:16][C:17]([C:19]1[S:20][C:21]([CH2:34][CH3:35])=[C:22]([C:24]2[CH:25]=[N:26][N:27]3[CH:32]=[C:31]([OH:37])[CH:30]=[N:29][C:28]=23)[CH:23]=1)=[O:18])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 89750974HCID 89750974, compound

Product 1

HCID 89750984HCID 89750984, compoundYield 74.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

tert-Butyl[(1R,2R)-2-({[4-(6-bromopyrazolo[1,5-a]pyrimidin-3-yl)-5-ethylthiophen-2-yl]carbonyl}amino)-3,3-difluorocyclohexyl]carbamate (0.151 g, 0.258 mmol) was dissolved in methanol (1.29 mL) and KOH (14.5 mg, 0.258 mmol) was added. The reaction was heated to 65° C. until conversion to the alcohol was complete. The reaction was then concentrated under reduced pressure. The remaining residue was mixed with dichloromethane, washed with saturated ammonium chloride (aq) twice and brine once. The organic layer was mixed with water and extracted 3× with dichloromethane. The combined organic layers were dried with sodium sulfate, filtered, and concentrated under reduced pressure to give the title compound (0.100 g, 0.192 mmol). LRMS (APCI) calc'd for (C24H29F2N5O4S) [M+H]+, 522.2. found 522.0.

Workup

  1. concentrationThe reaction was then concentrated under reduced pressure
  2. additionThe remaining residue was mixed with dichloromethane
  3. washwashed with saturated ammonium chloride (aq) twice
  4. additionThe organic layer was mixed with water
  5. extractionextracted 3× with dichloromethane
  6. dry with materialThe combined organic layers were dried with sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-4675f74bb9c34bc3a6d292b317471e6d
Source dataset
uspto-grants-2015_02
Patent number
US08946237B2

Reaction notes

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