Phenylacetaldehyde → HCID 86686767, compound

HRID 1403138Notes

Reaction equation

HRID 1403138 reaction equation
Cl.Cl.[F:3][CH:4]([F:32])[C:5]1[N:9]([C:10]2[CH:15]=[C:14]([N:16]3[CH2:21][CH2:20][O:19][CH2:18][CH2:17]3)[N:13]=[C:12]([NH:22][C@H:23]3[CH2:27][CH2:26][NH:25][CH2:24]3)[N:11]=2)[C:8]2[CH:28]=[CH:29][CH:30]=[CH:31][C:7]=2[N:6]=1.[C:33]1([CH2:39][CH:40]=O)[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)(O)[O-].[Na+]>C(O)(=O)C.CN(C)C=O>[F:32][CH:4]([F:3])[C:5]1[N:9]([C:10]2[CH:15]=[C:14]([N:16]3[CH2:21][CH2:20][O:19][CH2:18][CH2:17]3)[N:13]=[C:12]([NH:22][C@H:23]3[CH2:27][CH2:26][N:25]([CH2:40][CH2:39][C:33]4[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=4)[CH2:24]3)[N:11]=2)[C:8]2[CH:28]=[CH:29][CH:30]=[CH:31][C:7]=2[N:6]=1

Participants

7

Reactant 4

HCID 998PhenylacetaldehydeHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 86686768HCID 86686768, compound

Product 1

HCID 86686767HCID 86686767, compoundYield 48.6%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6228DimethylformamideSolvent

Procedure

To a mixture of 4-[2-(difluoromethyl)-1H-benzimidazol-1-yl]-6-morpholin-4-yl-N-[(3S)-pyrrolidin-3-yl]pyrimidin-2-amine dihydrochloride (58 mg) and N,N-dimethylformamide (1.2 mL) were added phenylacetaldehyde (21 mg), sodium triacetoxyborohydride (75 mg), and acetic acid (0.29 mL), and the mixture was stirred at room temperature overnight. To the reaction mixture was added a saturated aqueous sodium bicarbonate solution, followed by extraction with ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure and then the residue was purified by amino silica gel column chromatography (chloroform:methanol=100:0-90:10) to obtain 4-[2-(difluoromethyl)-1H-benzimidazol-1-yl]-6-morpholin-4-yl-N-[(3S)-1-(2-phenylethyl)pyrrolidin-3-yl]pyrimidin-2-amine (30 mg) as a white powder.

Workup

  1. extractionfollowed by extraction with ethyl acetate
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. customthe residue was purified by amino silica gel column chromatography (chloroform:methanol=100:0-90:10)

Sources & evidence

ORD record
ord-2b8841dedd9d45f4bd155f9f18301c08
Source dataset
uspto-grants-2014_12
Patent number
US08912180B2

Reaction notes

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