Sodium cyanoborohydride → HCID 56971090, compound

HRID 1519624Notes

Reaction equation

HRID 1519624 reaction equation
[CH3:1][O:2][C:3]1[CH:10]=[C:9]([CH2:11][CH2:12][N:13]2[CH2:18][CH2:17][NH:16][CH2:15][CH:14]2[C:19]([F:22])([F:21])[F:20])[CH:8]=[CH:7][C:4]=1[C:5]#[N:6].[O:23]=[C:24]1[C:28]2[CH:29]=[CH:30][C:31]([CH2:33][CH:34]=O)=[CH:32][C:27]=2[CH2:26][O:25]1.C([BH3-])#N.[Na+]>CO>[CH3:1][O:2][C:3]1[CH:10]=[C:9]([CH2:11][CH2:12][N:13]2[CH2:18][CH2:17][N:16]([CH2:34][CH2:33][C:31]3[CH:30]=[CH:29][C:28]4[C:24](=[O:23])[O:25][CH2:26][C:27]=4[CH:32]=3)[CH2:15][CH:14]2[C:19]([F:21])([F:22])[F:20])[CH:8]=[CH:7][C:4]=1[C:5]#[N:6]

Participants

5

Reactant 3

HCID 5003444Sodium cyanoborohydrideHCID 67514674HCID 67514674, compoundHCID 772312612-(1-Oxo-1,3-dihydroisobenzofuran-5-yl)acetaldehyde

Product 1

HCID 56971090HCID 56971090, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a mixture of 2-methoxy-4-{2-[2-(trifluoromethyl)piperazin-1-yl]ethyl}benzonitrile (116 mg, 0.28 mmol) and (1-oxo-1,3-dihydro-2-benzofuran-5-yl)acetaldehyde (49 mg, 0.28 mmol) in methanol (1.0 mL) at 0° C. was added sodium cyanoborohydride (18 mg, 0.28 mmol) and the mixture was stirred at room temperature for 12 hours. The reaction mixture was concentrated and purified by mass-directed HPLC to provide 2-methoxy-4-(2-{4-[2-(1-oxo-1,3-dihydro-2-benzofuran-5-yl)ethyl]-2-(trifluoromethyl)piperazin-1-yl}ethyl)benzonitrile. LC-MS (IE, m/z): 474.4 [M+1]+. (0.27 μM)

Workup

  1. concentrationThe reaction mixture was concentrated
  2. custompurified by mass-directed HPLC

Sources & evidence

ORD record
ord-589a9a0fcfe9424796ce6fbc920e3126
Source dataset
uspto-grants-2015_07
Patent number
US09073882B2

Reaction notes

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