Acetic Acid → 2-Chloro-4-(2-{2-oxo-4-[2-(1-oxo-1,3-dihydro-2-benzofuran-5-yl)ethyl]piperazin-1-yl}ethyl)benzonitrile

HRID 1466152Notes

Reaction equation

HRID 1466152 reaction equation
[Cl:1][C:2]1[CH:9]=[C:8]([CH2:10][CH2:11][N:12]2[CH2:17][CH2:16][NH:15][CH2:14][C:13]2=[O:18])[CH:7]=[CH:6][C:3]=1[C:4]#[N:5].[O:19]=[C:20]1[C:24]2[CH:25]=[CH:26][C:27]([CH2:29][CH:30]=O)=[CH:28][C:23]=2[CH2:22][O:21]1.[BH3-]C#N.[Na+].C(O)(=O)C>CO.C(Cl)Cl>[Cl:1][C:2]1[CH:9]=[C:8]([CH2:10][CH2:11][N:12]2[CH2:17][CH2:16][N:15]([CH2:30][CH2:29][C:27]3[CH:26]=[CH:25][C:24]4[C:20](=[O:19])[O:21][CH2:22][C:23]=4[CH:28]=3)[CH2:14][C:13]2=[O:18])[CH:7]=[CH:6][C:3]=1[C:4]#[N:5]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 5003444Sodium cyanoborohydrideHCID 772312612-(1-Oxo-1,3-dihydroisobenzofuran-5-yl)acetaldehydeHCID 895249932-Chloro-4-[2-(2-oxopiperazin-1-yl)ethyl]benzonitrile

Product 1

HCID 895334702-Chloro-4-(2-{2-oxo-4-[2-(1-oxo-1,3-dihydro-2-benzofuran-5-yl)ethyl]piperazin-1-yl}ethyl)benzonitrile

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of 2-Chloro-4-[2-(2-oxopiperazin-1-yl)ethyl]benzonitrile (70 mg, 0.265 mmol), (1-Oxo-1,3-dihydro-2-benzofuran-5-yl)acetaldehyde (82 mg, 0.466 mmol), NaBH3CN (43 mg, 0.68 mmol) and acetic acid (28 mg, 0.466 mmol) in methanol (2 mL) and DCM (2 mL) was stirred at RT for 3 hours. Then the mixture was purified by prep-TLC to give the title product. 1H-NMR (MeOD, 400 MHz) δ ppm 7.83 (d, J=7.6 Hz, 1H), 7.71 (d, J=7.6 Hz, 1H), 7.58 (d, J=1.6 Hz, 1H), 7.54 (s, 1H), 7.50 (d, J=7.6 Hz, 1H), 7.38 (dd, J=1.6, 7.6 Hz, 1H), 5.36 (s, 2H), 3.78 (s, 2H), 3.68 (t, J=7.2 Hz, 2H), 3.56 (t, J=5.6 Hz, 2H), 3.40-3.42 (m, 2H), 3.30-3.33 (m, 2h), 3.13-3.18 (m, 2H), 2.98 (t, J=7.6 Hz, 2H).

Workup

  1. customThen the mixture was purified by prep-TLC

Sources & evidence

ORD record
ord-493d43a032c94f8494323b841150476a
Source dataset
uspto-grants-2015_04
Patent number
US08999990B2

Reaction notes

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