4-(Dimethylamino)benzoyl chloride → HCID 58342138, compound

HRID 339576Notes

Reaction equation

HRID 339576 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([CH:8]=[C:9]([C:11]3[CH:17]=[CH:16][C:14]([NH2:15])=[CH:13][CH:12]=3)[N:10]=2)[CH:7]=1.[CH3:18][N:19]([CH3:29])[C:20]1[CH:28]=[CH:27][C:23]([C:24](Cl)=[O:25])=[CH:22][CH:21]=1.C(Cl)Cl.CCOC(C)=O>N1C=CC=CC=1>[CH3:18][N:19]([CH3:29])[C:20]1[CH:28]=[CH:27][C:23]([C:24]([NH:15][C:14]2[CH:16]=[CH:17][C:11]([C:9]3[N:10]=[C:5]4[CH:4]=[CH:3][C:2]([F:1])=[CH:7][N:6]4[CH:8]=3)=[CH:12][CH:13]=2)=[O:25])=[CH:22][CH:21]=1

Participants

5

Reactant 3

HCID 44007824-(Dimethylamino)benzoyl chlorideHCID 21226138Dichloromethane ethylacetateHCID 23106705HCID 23106705, compound

Product 1

HCID 58342138HCID 58342138, compoundYield 36%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Prepared as described in the Amide Coupling section using 4-(6-fluoroimidazo[1,2-a]pyridin-2-yl)aniline (100 mg, 0.44 mmol) and 4-dimethylaminobenzoyl chloride (81 mg, 0.44 mmol) in dry pyridine (5 ml) to give the title compound (59 mg, 36%) as a pale yellow solid after work-up and flash chromatography (1:1 DCM/EtOAc).

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-0eaad7b47f8145db94cc53c2176a9eea
Source dataset
uspto-grants-2014_11
Patent number
US08895313B2

Reaction notes

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