Acetyl chloride → HCID 73296750, compound

HRID 623764Notes

Reaction equation

HRID 623764 reaction equation
Cl.[NH2:2][CH2:3][CH2:4][N:5]([CH3:32])[C:6]([C:8]1[N:9]([CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[C:10]([C:21]([F:24])([F:23])[F:22])=[C:11]([CH3:20])[C:12]=1[C:13]1[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][CH:14]=1)=[O:7].CCN(CC)CC.[C:40](Cl)(=[O:42])[CH3:41]>C(Cl)Cl.C([O-])(O)=O.[Na+]>[C:40]([NH:2][CH2:3][CH2:4][N:5]([CH3:32])[C:6]([C:8]1[N:9]([CH2:25][C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=2)[C:10]([C:21]([F:23])([F:24])[F:22])=[C:11]([CH3:20])[C:12]=1[C:13]1[CH:14]=[CH:15][C:16]([Cl:19])=[CH:17][CH:18]=1)=[O:7])(=[O:42])[CH3:41]

Participants

6

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 86711847HCID 86711847, compound

Product 1

HCID 73296750HCID 73296750, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 516892Sodium BicarbonateSolvent

Procedure

To a suspension of N-(2-aminoethyl)-1-benzyl-3-(4-chlorophenyl)-N,4-dimethyl-5-(trifluoromethyl)-1H-pyrrole-2-carboxamide hydrochloride (150 mg, 0.308 mmol) in DCM (2 mL) were added dropwise Et3N (0.094 mL, 0.679 mmol) and acetyl chloride (0.024 mL, 0.339 mmol). The reaction mixture was stirred at room temperature overnight. The mixture was diluted with DCM and saturated aqueous NaHCO3. The layers were separated using a phase separator and the solvents were evaporated. The product was purified by flash column chromatography (silica, gradient heptane/EtOAc, 1:2→0:1) to afford 106 mg (70%) of SC-37.

Workup

  1. customThe layers were separated
  2. customthe solvents were evaporated
  3. customThe product was purified by flash column chromatography (silica, gradient heptane/EtOAc, 1:2→0:1)
  4. customto afford 106 mg (70%) of SC-37

Sources & evidence

ORD record
ord-d4466f3fe5f149e2a4eaae7ab92d81ca
Source dataset
uspto-grants-2016_04
Patent number
US09302988B2

Reaction notes

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