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

HRID 1519621Notes

Reaction equation

HRID 1519621 reaction equation
[CH3:1][C:2]1[C:10]2[CH2:9][O:8][C:7](=[O:11])[C:6]=2[CH:5]=[CH:4][C:3]=1[CH:12]([CH3:20])[CH2:13][N:14]1[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]1.[CH3:21][O:22][C:23]1[CH:30]=[C:29]([CH2:31][CH:32]=O)[CH:28]=[CH:27][C:24]=1[C:25]#[N:26].C([BH3-])#N.[Na+]>CO>[CH3:21][O:22][C:23]1[CH:30]=[C:29]([CH2:31][CH2:32][N:17]2[CH2:18][CH2:19][N:14]([CH2:13][CH:12]([C:3]3[CH:4]=[CH:5][C:6]4[C:7](=[O:11])[O:8][CH2:9][C:10]=4[C:2]=3[CH3:1])[CH3:20])[CH2:15][CH2:16]2)[CH:28]=[CH:27][C:24]=1[C:25]#[N:26]

Participants

5

Reactant 3

HCID 5003444Sodium cyanoborohydrideHCID 595686964-Methyl-5-(1-methyl-2-piperazin-1-ylethyl)-2-benzofuran-1(3H)-oneHCID 772312592-(Methyloxy)-4-(2-oxoethyl)benzonitrile

Product 1

HCID 680716722-Methoxy-4-(2-{4-[2-(4-methyl-1-oxo-1,3-dihydro-2-benzofuran-5-yl)propyl]piperazin-1-yl}ethyl)benzonitrile

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a mixture of 4-methyl-5-[1-(piperazin-1-yl)propan-2-yl]-2-benzofuran-1(3H)-one (25 mg, 0.080 mmol) and 2-methoxy-4-(2-oxoethyl)benzonitrile (17 mg, 0.097 mmol) in methanol (1.0 mL) at 0° C. was added sodium cyanoborohydride (7 mg, 0.113 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-(4-methyl-1-oxo-1,3-dihydro-2-benzofuran-5-yl)propyl]piperazin-1-yl}ethyl)benzonitrile. LC-MS (IE, m/z): 434.3 [M+1]+. (0.17 μM)

Workup

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

Sources & evidence

ORD record
ord-624a63f1629047739bdc54556f87d33e
Source dataset
uspto-grants-2015_07
Patent number
US09073882B2

Reaction notes

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