Water → (RS)-1-[5-(4-Fluoro-phenyl)-2-methyl-thiazol-4-yl]-1-{2-[4-(1-hydroxy-ethyl)-1H-benzoimidazol-2-ylmethyl]-piperidin-1-yl}-methanone

HRID 1367042Notes

Reaction equation

HRID 1367042 reaction equation
[BH4-].[Na+].[C:3]([C:6]1[C:14]2[N:13]=[C:12]([CH2:15][CH:16]3[CH2:21][CH2:20][CH2:19][CH2:18][N:17]3[C:22]([C:24]3[N:25]=[C:26]([CH3:36])[S:27][C:28]=3[C:29]3[CH:34]=[CH:33][C:32]([F:35])=[CH:31][CH:30]=3)=[O:23])[NH:11][C:10]=2[CH:9]=[CH:8][CH:7]=1)(=[O:5])[CH3:4].O>CO>[F:35][C:32]1[CH:31]=[CH:30][C:29]([C:28]2[S:27][C:26]([CH3:36])=[N:25][C:24]=2[C:22]([N:17]2[CH2:18][CH2:19][CH2:20][CH2:21][CH:16]2[CH2:15][C:12]2[NH:11][C:10]3[CH:9]=[CH:8][CH:7]=[C:6]([CH:3]([OH:5])[CH3:4])[C:14]=3[N:13]=2)=[O:23])=[CH:34][CH:33]=1

Participants

5

Reactant 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 17973678(RS)-1-[2-(4-Acetyl-1H-benzoimidazol-2-ylmethyl)-piperidin-1-yl]-1-[5-(4-fluorophenyl)-2-methylthiazol-4-yl]methanone

Product 1

HCID 66967896(RS)-1-[5-(4-Fluoro-phenyl)-2-methyl-thiazol-4-yl]-1-{2-[4-(1-hydroxy-ethyl)-1H-benzoimidazol-2-ylmethyl]-piperidin-1-yl}-methanone

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Sodium borohydride (145 mg) was added portionwise over 2 min. to a cooled (0-10° C.) solution of (RS)-1-[2-(4-acetyl-1H-benzimidazol-2-ylmethyl)-piperidin-1-yl]-1-[5-(4-fluorophenyl)-2-methylthiazol-4-yl]methanone, E68 (365 mg) in methanol (10 ml). After stirring for a further 2.5 h at room temperature, water (100 ml) was added and the mixture was extracted with dichloromethane (2×). The combined organics were dried (Na2SO4), evaporated and the residue chromatographed (silica gel, 0-100% ethyl acetate-hexane then 2-10% methanol-ethyl acetate) to afford the title compound as a solid (320 mg).

Workup

  1. extractionthe mixture was extracted with dichloromethane (2×)
  2. dry with materialThe combined organics were dried (Na2SO4)
  3. customevaporated
  4. customthe residue chromatographed (silica gel, 0-100% ethyl acetate-hexane

Sources & evidence

ORD record
ord-4cbf5db37d59429fbb74e5dd09037558
Source dataset
uspto-grants-2011_02
Patent number
US07893090B2

Reaction notes

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