Sodium cyanoborohydride → HCID 67516957, compound

HRID 1519617Notes

Reaction equation

HRID 1519617 reaction equation
[F:1][C:2]([F:22])([F:21])[CH:3]1[CH2:8][NH:7][CH2:6][CH2:5][N:4]1[CH2:9][CH2:10][C:11]1[CH:20]=[CH:19][C:14]2[C:15](=[O:18])[O:16][CH2:17][C:13]=2[CH:12]=1.[CH3:23][O:24][C:25]1[CH:32]=[C:31]([CH2:33][CH:34]=O)[CH:30]=[CH:29][C:26]=1[C:27]#[N:28].C([BH3-])#N.[Na+]>CO>[CH3:23][O:24][C:25]1[CH:32]=[C:31]([CH2:33][CH2:34][N:7]2[CH2:6][CH2:5][N:4]([CH2:9][CH2:10][C:11]3[CH:20]=[CH:19][C:14]4[C:15](=[O:18])[O:16][CH2:17][C:13]=4[CH:12]=3)[CH:3]([C:2]([F:1])([F:21])[F:22])[CH2:8]2)[CH:30]=[CH:29][C:26]=1[C:27]#[N:28]

Participants

5

Reactant 3

HCID 5003444Sodium cyanoborohydrideHCID 69087509HCID 69087509, compoundHCID 772312592-(Methyloxy)-4-(2-oxoethyl)benzonitrile

Product 1

HCID 67516957HCID 67516957, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a mixture of 5-{2-[2-(trifluoromethyl)piperazin-1-yl]ethyl}-2-benzofuran-1(3H)-one (95 mg, 0.27 mmol) and 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 2-methoxy-4-(2-{4-[2-(1-oxo-1,3-dihydro-2-benzofuran-5-yl)ethyl]-3-(trifluoromethyl)piperazin-1-yl}ethyl)benzonitrile. LC-MS (IE, m/z): 474.3 [M+1]+. 1H-NMR (500 MHz, CD3OD) δ ppm 7.82 (m, 1H), 7.60 (overlapping m's, 3H), 7.15 (s, 1H), 7.02 (m, 1H), 5.38 (s, 2H), 3.98 (s, 3H), 3.90 (m, 1H), 3.58 (m, 2H), 3.51 (m, 2H), 3.43 (m, 2H), 3.20 (m, 4H), 3.12 (m, 2H), 3.08 (m, 2H). (0.65 μM)

Workup

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

Sources & evidence

ORD record
ord-f76a644582ab45b2be8972a199631db8
Source dataset
uspto-grants-2015_07
Patent number
US09073882B2

Reaction notes

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