Acetyl chloride → HCID 67262174, compound

HRID 1028098Notes

Reaction equation

HRID 1028098 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([N:21]([C:29]2[N:34]=[C:33]([C:35]([F:38])([F:37])[F:36])[CH:32]=[CH:31][N:30]=2)[C:22](=[O:28])[O:23][C:24]([CH3:27])([CH3:26])[CH3:25])[CH:5]=[C:6]([C:8]2[S:12][C:11]([N:13]3[CH2:19][CH2:18][CH2:17][NH:16][C:15](=[O:20])[CH2:14]3)=[N:10][CH:9]=2)[CH:7]=1.C(N(CC)CC)C.[C:46](Cl)(=[O:48])[CH3:47]>ClCCl.C(OCC)(=O)C>[C:46]([NH:1][C:2]1[CH:3]=[C:4]([N:21]([C:29]2[N:34]=[C:33]([C:35]([F:36])([F:37])[F:38])[CH:32]=[CH:31][N:30]=2)[C:22](=[O:28])[O:23][C:24]([CH3:26])([CH3:27])[CH3:25])[CH:5]=[C:6]([C:8]2[S:12][C:11]([N:13]3[CH2:19][CH2:18][CH2:17][NH:16][C:15](=[O:20])[CH2:14]3)=[N:10][CH:9]=2)[CH:7]=1)(=[O:48])[CH3:47]

Participants

6

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 86674324HCID 86674324, compound

Product 1

HCID 67262174HCID 67262174, compoundYield 60%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a suspension of tert-butyl {3-amino-5-[2-(3-oxo-1,4-diazepan-1-yl)-1,3-thiazol-5-yl]phenyl}[4-(trifluoromethyl)pyrimidin-2-yl]carbamate (125 mg, 0.227 mmol) in dichloromethane (2.5 mL) at room temperature, under nitrogen, was added triethylamine (0.079 mL, 0.569 mmol) and acetyl chloride (0.024 mL, 0.341 mmol). The mixture was stirred at room temperature for 18 h after which time a solution was obtained. The mixture was diluted with ethyl acetate and washed with water and brine, and dried over sodium sulfate. Silica gel (1 g) was added and the solution concentrated to dryness. The resulting solid was purified by silica gel chromatography (ethanol/dichloromethane eluant) to afford 80 mg (0.135 mmol, 60% yield) of tert-butyl {3-(acetylamino)-5-[2-(3-oxo-1,4-diazepan-1-yl)-1,3-thiazol-5-yl]phenyl}[4-(trifluoromethyl)pyrimidin-2-yl]carbamate as an off-white solid.

Workup

  1. customwas obtained
  2. washwashed with water and brine
  3. dry with materialdried over sodium sulfate
  4. additionSilica gel (1 g) was added
  5. concentrationthe solution concentrated to dryness
  6. customThe resulting solid was purified by silica gel chromatography (ethanol/dichloromethane eluant)

Sources & evidence

ORD record
ord-ba17ab2f2f774260bcb0be809ad0f37c
Source dataset
uspto-grants-2014_05
Patent number
US08735417B2

Reaction notes

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