Acetyl chloride → HCID 22063877, compound

HRID 1828211Notes

Reaction equation

HRID 1828211 reaction equation
[NH2:1][C:2]1[N:6]([CH3:7])[N:5]=[C:4]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[C:3]=1[C:14]1[CH:28]=[CH:27][C:17]2[N:18]([CH:23]3[CH2:26][CH2:25][CH2:24]3)[C:19](=[O:22])[N:20]([CH3:21])[C:16]=2[CH:15]=1.C(N(CC)CC)C.[C:36](Cl)(=[O:38])[CH3:37]>C(Cl)(Cl)Cl.C(=O)(O)[O-].[Na+]>[NH2:1][C:2]1[N:6]([CH3:7])[N:5]=[C:4]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[C:3]=1[C:14]1[CH:28]=[CH:27][C:17]2[N:18]([CH:23]3[CH2:26][CH2:25][CH2:24]3)[C:19](=[O:22])[N:20]([CH3:21])[C:16]=2[CH:15]=1.[CH:23]1([N:18]2[C:17]3[CH:27]=[CH:28][C:14]([C:3]4[C:4]([C:8]5[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=5)=[N:5][N:6]([CH3:7])[C:2]=4[NH:1][C:36](=[O:38])[CH3:37])=[CH:15][C:16]=3[N:20]([CH3:21])[C:19]2=[O:22])[CH2:26][CH2:25][CH2:24]1

Participants

7

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 22063877HCID 22063877, compound

Product 2

HCID 22063877HCID 22063877, compoundHCID 22064000HCID 22064000, compound

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 516892Sodium BicarbonateSolvent

Procedure

5-(5-Amino-1-methyl-3-phenyl-1H-pyrazol-4-yl)-1-cyclobutyl-3-methyl-1,3-dihydro-benzoimidazol-2-one is prepared according to the methods described in Example 336. 5-(5-Amino-1-methyl-3-phenyl-1H-pyrazol-4-yl)-1-cyclobutyl-3-methyl-1,3-dihydro-benzoimidazol-2-one (0.05 g) is diluted with chloroform (0.5 mL) and is treated with triethyl amine (0.04 mL) and acetyl chloride (0.02 mL). The reaction is allowed to stir for 1 hour then is diluted with saturated sodium bicarbonate and extracted with ethyl acetate. After concentration of the organic layer the product is purified by silica gel chromatography to give N-[4-(1-Cyclobutyl-3-methyl-2-oxo-2,3-dihydro-1H-benzoimidazol-5-yl)-2-methyl-5-phenyl-2H-pyrazol-3-yl]-acetamide. Similar reaction conditions utilizing the appropriate isocyanate, chloroformate or sulfonyl halide can be used to prepare ureas, carbamates and sulfonamides.

Workup

  1. extractionextracted with ethyl acetate
  2. customAfter concentration of the organic layer the product is purified by silica gel chromatography

Sources & evidence

ORD record
ord-7344ef755b404cc5a58793a80becc6f2
Source dataset
uspto-grants-2006_06
Patent number
US07056918B2

Reaction notes

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