Acetyl chloride → HCID 67538191, compound

HRID 2240948Notes

Reaction equation

HRID 2240948 reaction equation
[NH2:1][C:2]1[N:6]([CH3:7])[C:5](=[O:8])[C:4]([C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([NH2:25])[CH:20]=2)([C:9]2[CH:14]=[CH:13][C:12]([O:15][CH:16]([F:18])[F:17])=[CH:11][CH:10]=2)[N:3]=1.[C:26]([Cl:29])(=[O:28])[CH3:27].CCN(CC)CC>C1COCC1>[ClH:29].[NH2:1][C:2]1[N:6]([CH3:7])[C:5](=[O:8])[C:4]([C:19]2[CH:20]=[C:21]([NH:25][C:26](=[O:28])[CH3:27])[CH:22]=[CH:23][CH:24]=2)([C:9]2[CH:14]=[CH:13][C:12]([O:15][CH:16]([F:17])[F:18])=[CH:11][CH:10]=2)[N:3]=1

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 25123323HCID 25123323, compound

Product 1

HCID 67538191HCID 67538191, compoundYield 43%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 2-amino-5-(3-amino-phenyl)-5-(4-difluoromethoxy-phenyl)-3-methyl-3,5-dihydro-imidazol-4-one (88 mg, 0.25 mmol), acetyl chloride (20 mg, 0.25 mmol), NEt3 (51 mg, 0.51 mmol) in THF (2.5 mL) was stirred at rt for 1 h, concentrated and purified by reverse-phase HPLC followed by treatment with hydrochloric acid to provide the title compound (42 mg, 43%), characterized by NMR and mass spectral analyses. MS (ES+) m/e 389 (M+H)+.

Workup

  1. concentrationconcentrated
  2. custompurified by reverse-phase HPLC

Sources & evidence

ORD record
ord-1c3d5e0fc39a4c7c893832d664ff2892
Source dataset
uspto-grants-2010_05
Patent number
US07723368B2

Reaction notes

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