Benzoyl chloride, 3-chloro- → HCID 67344271, compound

HRID 1846654Notes

Reaction equation

HRID 1846654 reaction equation
[NH2:1][C:2]1[C:3]([N:9]2[CH2:14][CH2:13][CH:12]([CH2:15][C:16]([N:18]3[CH2:24][CH2:23][CH2:22][N:21]([CH3:25])[CH2:20][CH2:19]3)=[O:17])[CH2:11][CH2:10]2)=[N:4][CH:5]=[C:6]([Br:8])[CH:7]=1.[Cl:26][C:27]1[CH:28]=[C:29]([CH:33]=[CH:34][CH:35]=1)[C:30](Cl)=[O:31]>C(#N)C>[Br:8][C:6]1[CH:7]=[C:2]([NH:1][C:30](=[O:31])[C:29]2[CH:33]=[CH:34][CH:35]=[C:27]([Cl:26])[CH:28]=2)[C:3]([N:9]2[CH2:10][CH2:11][CH:12]([CH2:15][C:16]([N:18]3[CH2:24][CH2:23][CH2:22][N:21]([CH3:25])[CH2:20][CH2:19]3)=[O:17])[CH2:13][CH2:14]2)=[N:4][CH:5]=1

Participants

4

Reactant 2

HCID 69252Benzoyl chloride, 3-chloro-HCID 67342749HCID 67342749, compound

Product 1

HCID 67344271HCID 67344271, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 0.350 g (0.853 mmol) of 2-(3′-amino-5′-bromo-3,4,5,6-tetrahydro-2H-[1,2′]bipyridinyl-4-yl)-1-(4-methyl-[1,4]diazepan-1-yl)-ethanone in acetonitrile (50 mL) is added 0.15 g (0.853 mmol) of 3-chlorobenzoyl chloride. The mixture is stirred overnight at room temperature during which time a solid precipitates from solution. The formed solid is collected by filtration, washed with cold diethyl ether and dried on the filter pad to provide 0.308 g (66.0%) of N-{5′-bromo-4-[2-(4-methyl-[1,4]diazepan-1-yl)-2-oxo-ethyl]-3,4,5,6-tetrahydro-2H-[1,2′]bipyridinyl-3′-yl}-3-chloro-benzamide in N,N-dimethylformamide as a white solid.

Workup

  1. customprecipitates from solution
  2. filtrationThe formed solid is collected by filtration
  3. washwashed with cold diethyl ether
  4. customdried on the filter pad

Sources & evidence

ORD record
ord-3eb976cde7a24564b258d9e1414511e8
Source dataset
uspto-grants-2015_02
Patent number
US08952004B2

Reaction notes

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