Sodium Bicarbonate → HCID 86648392, compound

HRID 409443Notes

Reaction equation

HRID 409443 reaction equation
[F:1][C:2]([F:47])([F:46])[C:3]1[CH:4]=[C:5]([CH:39]=[C:40]([C:42]([F:45])([F:44])[F:43])[CH:41]=1)[CH2:6][N:7]([C:27]1[N:32]=[CH:31][C:30]([C:33]2[CH:34]=[N:35][N:36]([CH3:38])[CH:37]=2)=[CH:29][N:28]=1)[C@@H:8]1[CH2:12][N:11]([C:13]2[CH:20]=[CH:19][C:18]([C:21]([F:24])([F:23])[F:22])=[CH:17][C:14]=2[CH:15]=[O:16])[C@H:10]([CH2:25][CH3:26])[CH2:9]1.[BH4-].[Na+].C(=O)([O-])O.[Na+]>CO>[F:46][C:2]([F:1])([F:47])[C:3]1[CH:4]=[C:5]([CH:39]=[C:40]([C:42]([F:45])([F:44])[F:43])[CH:41]=1)[CH2:6][N:7]([C:27]1[N:32]=[CH:31][C:30]([C:33]2[CH:34]=[N:35][N:36]([CH3:38])[CH:37]=2)=[CH:29][N:28]=1)[C@@H:8]1[CH2:12][N:11]([C:13]2[CH:20]=[CH:19][C:18]([C:21]([F:22])([F:23])[F:24])=[CH:17][C:14]=2[CH2:15][OH:16])[C@H:10]([CH2:25][CH3:26])[CH2:9]1

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 4311764Sodium borohydrideHCID 59614338HCID 59614338, compound

Product 1

HCID 86648392HCID 86648392, compoundYield 97.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a mixture of 2-((2R,4S)-4-{[3,5-bis(trifluoromethyl)benzyl]-[5-(1-methyl-1H-pyrazol-4-yl)-pyrimidin-2-yl]-amino}-2-ethyl-pyrrolidin-1-yl)-5-trifluoromethyl-benzaldehyde (75 mg, 0.11 mmol) in MeOH (2.0 mL) is added sodium borohydride (6 mg, 0.17 mmol). The reaction mixture is stirred at room temperature for 15 minutes. After addition of saturated aqueous sodium hydrogen carbonate, and the mixture is extracted with EtOAc. The combined organic layer is dried over MgSO4 then concentrated under reduced pressure. The obtained residue is purified by silica gel column chromatography (eluent: n-hexane/EtOAc) to give [2-((2R,4S)-4-{[3,5-bis(trifluoromethyl)benzyl]-[5-(1-methyl-1H-pyrazol-4-yl)-pyrimidin-2-yl]-amino}-2-ethyl-pyrrolidin-1-yl)-5-trifluoromethyl-phenyl]-methanol as a colorless oil (72 mg, 96%). ESI-MS m/z: 672 [M+1]+, Retention time 2.36 min (condition A).

Workup

  1. extractionthe mixture is extracted with EtOAc
  2. dry with materialThe combined organic layer is dried over MgSO4
  3. concentrationthen concentrated under reduced pressure
  4. customThe obtained residue is purified by silica gel column chromatography (eluent: n-hexane/EtOAc)

Sources & evidence

ORD record
ord-59f50b962b9f4d3eb69b3ca033fd49b1
Source dataset
uspto-grants-2014_06
Patent number
US08759365B2

Reaction notes

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