Sodium cyanoborohydride → 5-Fluoro-2-methoxy-4-(2-{4-[2-(4-methyl-1-oxo-1,3-dihydro-2-benzofuran-5-yl)ethyl]piperazin-1-yl}ethyl)benzonitrile

HRID 1519619Notes

Reaction equation

HRID 1519619 reaction equation
[N:1]1([CH2:7][CH2:8][C:9]2[CH:18]=[CH:17][C:12]3[C:13](=[O:16])[O:14][CH2:15][C:11]=3[CH:10]=2)[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.[F:19][C:20]1[C:21]([CH2:30][CH:31]=O)=[CH:22][C:23]([O:28][CH3:29])=[C:24]([CH:27]=1)[C:25]#[N:26].[C:33]([BH3-])#N.[Na+]>CO>[F:19][C:20]1[C:21]([CH2:30][CH2:31][N:4]2[CH2:5][CH2:6][N:1]([CH2:7][CH2:8][C:9]3[CH:18]=[CH:17][C:12]4[C:13](=[O:16])[O:14][CH2:15][C:11]=4[C:10]=3[CH3:33])[CH2:2][CH2:3]2)=[CH:22][C:23]([O:28][CH3:29])=[C:24]([CH:27]=1)[C:25]#[N:26]

Participants

5

Reactant 3

HCID 5003444Sodium cyanoborohydrideHCID 595686715-[2-(piperazin-1-yl)ethyl]-2-benzofuran-1(3H)-oneHCID 866944585-Fluoro-2-methoxy-4-(2-oxoethyl)benzonitrile

Product 1

HCID 680718865-Fluoro-2-methoxy-4-(2-{4-[2-(4-methyl-1-oxo-1,3-dihydro-2-benzofuran-5-yl)ethyl]piperazin-1-yl}ethyl)benzonitrile

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a mixture of 5-[2-(piperazin-1-yl)ethyl]-2-benzofuran-1(3H)-one (95 mg, 0.27 mmol) and 5-fluoro-2-methoxy-4-(2-oxoethyl)benzonitrile (40 mg, 0.23 mmol) in methanol (1.0 mL) at 0° C. was added sodium cyanoborohydride (20 mg, 0.32 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 5-fluoro-2-methoxy-4-(2-{4-[2-(4-methyl-1-oxo-1,3-dihydro-2-benzofuran-5-yl)ethyl]piperazin-1-yl}ethyl)benzonitrile. LC-MS (IE, m/z): 438.4 [M+1]+. (0.034 μM)

Workup

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

Sources & evidence

ORD record
ord-2e32292d4b834c6cba262b0bcb2eeb55
Source dataset
uspto-grants-2015_07
Patent number
US09073882B2

Reaction notes

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