Water → HCID 58452660, compound

HRID 70602Notes

Reaction equation

HRID 70602 reaction equation
[BH4-].[Na+].[Cl:3][C:4]1[CH:5]=[C:6](/[C:19](/[C:27]2[NH:32][C:31](=[O:33])[C:30]([C:34]([F:37])([F:36])[F:35])=[CH:29][CH:28]=2)=[CH:20]\[C@H:21]2[CH2:25][CH2:24][C:23](=[O:26])[CH2:22]2)[CH:7]=[CH:8][C:9]=1[O:10][CH2:11][CH2:12][CH2:13][N:14]([CH2:17][CH3:18])[CH2:15][CH3:16].O>CO.[Cl-].[Na+].O>[Cl:3][C:4]1[CH:5]=[C:6](/[C:19](/[C:27]2[NH:32][C:31](=[O:33])[C:30]([C:34]([F:37])([F:35])[F:36])=[CH:29][CH:28]=2)=[CH:20]\[C@H:21]2[CH2:25][CH2:24][CH:23]([OH:26])[CH2:22]2)[CH:7]=[CH:8][C:9]=1[O:10][CH2:11][CH2:12][CH2:13][N:14]([CH2:15][CH3:16])[CH2:17][CH3:18]

Participants

6

Reactant 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 58452455HCID 58452455, compound

Product 1

HCID 58452660HCID 58452660, compoundYield 34%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

Sodium borohydride (4.4 mg) was added to a solution of 6-{(E)-1-{3-chloro-4-[3-(diethylamino)propoxy]phenyl}-2-[(1S)-3-oxocyclopentyl]ethenyl}-3-(trifluoromethyl)pyridin-2(1H)-one obtained in Example 1-83 (30 mg) in methanol (0.15 mL) at room temperature, and the mixture was stirred at room temperature for 30 minutes. Water and brine were added to the reaction solution, followed by extraction with chloroform. The organic layer was dried over anhydrous magnesium sulfate and filtered, after which the solvent was evaporated under reduced pressure. The residue was washed with diethyl ether to give the title compound (10 mg, 34%) as a pale yellow solid.

Workup

  1. extractionfollowed by extraction with chloroform
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. filtrationfiltered
  4. customafter which the solvent was evaporated under reduced pressure
  5. washThe residue was washed with diethyl ether

Sources & evidence

ORD record
ord-20cb69522964425a9afdf591cc4a5564
Source dataset
uspto-grants-2014_09
Patent number
US08822503B2

Reaction notes

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