Sodium cyanoborohydride → HCID 68071791, compound

HRID 1519632Notes

Reaction equation

HRID 1519632 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.[BH3-]C#N.[Na+].[Cl:23][C:24]1[C:25]([CH2:34][CH:35]=O)=[CH:26][C:27]([O:32][CH3:33])=[C:28]([CH:31]=1)[C:29]#[N:30]>C(Cl)Cl>[Cl:23][C:24]1[C:25]([CH2:34][CH2:35][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[CH:10]=3)[CH2:2][CH2:3]2)=[CH:26][C:27]([O:32][CH3:33])=[C:28]([CH:31]=1)[C:29]#[N:30]

Participants

5

Reactant 3

HCID 5003444Sodium cyanoborohydrideHCID 595686715-[2-(piperazin-1-yl)ethyl]-2-benzofuran-1(3H)-oneHCID 77230696HCID 77230696, compound

Product 1

HCID 68071791HCID 68071791, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of 5-(2-piperazin-1-ylethyl)-2-benzofuran-1(3H)-one (90 mg, 0.190 mmol) and NaBH3CN (24 mg, 0.380 mmol) in 20 mL DCM was added 5-chloro-2-methoxy-4-(2-oxoethyl)benzonitrile (40 mg, 0.190 mmol) and the mixture was stirred at RT overnight. Concentrated, and the residue was purified by prep-TLC to give 5-chloro-2-methoxy-4-(2-{4-[2-(1-oxo-1,3-dihydro-2-benzofuran-5-yl)ethyl]piperazin-1-yl}ethyl)benzonitrile. 1H-NMR (400 MHz, MeOD) δ ppm 7.82 (d, J=7.8 Hz, 1H), 7.67 (s, 1H), 7.50˜7.53 (m, 2H), 7.20 (s, 1H), 5.35 (s, 2H), 3.95 (s, 3H), 3.23˜3.26 (m, 6H), 3.10˜3.16 (m, 8H), 3.00˜3.03 (m, 2H). MS m/e 441 (M+1)+. (0.094 μM)

Workup

  1. concentrationConcentrated
  2. customthe residue was purified by prep-TLC

Sources & evidence

ORD record
ord-4604b9d6bc9f46d192b0c4c894cf52af
Source dataset
uspto-grants-2015_07
Patent number
US09073882B2

Reaction notes

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