Acetyl chloride → HCID 57900320, compound

HRID 84546Notes

Reaction equation

HRID 84546 reaction equation
[NH2:1][CH2:2][CH2:3][N:4]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=1[Cl:27])[C:5]([C:7]1[S:20][C:10]2[C:11]3[CH:19]=[CH:18][CH:17]=[CH:16][C:12]=3[O:13][CH2:14][CH2:15][C:9]=2[CH:8]=1)=[O:6].CCN(C(C)C)C(C)C.[C:37](Cl)(=[O:39])[CH3:38]>C(Cl)Cl>[C:37]([NH:1][CH2:2][CH2:3][N:4]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=1[Cl:27])[C:5]([C:7]1[S:20][C:10]2[C:11]3[CH:19]=[CH:18][CH:17]=[CH:16][C:12]=3[O:13][CH2:14][CH2:15][C:9]=2[CH:8]=1)=[O:6])(=[O:39])[CH3:38]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 81531DiisopropylethylamineHCID 57900372N-(2-aminoethyl)-N-(2-chlorophenyl)-4,5-dihydrobenzo[b]thieno[2,3-d]oxepine-2-carboxamide

Product 1

HCID 57900320HCID 57900320, compoundYield 18%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of N-(2-aminoethyl)-N-(2-chlorophenyl)-4,5-dihydrobenzo[b]thieno[2,3-d]oxepine-2-carboxamide 131 (0.300 g, 0.6 mmol) in methylene chloride (1.5 ml) was added DIEA (0.262 ml, 1.5 mmol). The reaction mixture was cooled with an ice water bath and acetyl chloride (0.0944 g, 1.2 mmol) was added drop-wise via syringe. The reaction mixture was stirred at cool temperature for 30 minutes and equilibrated to room temperature. The reaction mixture was washed with water, then saline and concentrated to a solid. The crude solid was taken into DMF and purified by RP-HPLC to give 46 mg of 258 (yield 18% of theoretical). MS: (ESI+) 441.1

Workup

  1. temperatureThe reaction mixture was cooled with an ice water bath
  2. temperatureat cool temperature for 30 minutes
  3. customequilibrated to room temperature
  4. washThe reaction mixture was washed with water
  5. concentrationsaline and concentrated to a solid
  6. custompurified by RP-HPLC

Sources & evidence

ORD record
ord-8c94ca6c3b5c48bab8cc048a2e9739fc
Source dataset
uspto-grants-2014_09
Patent number
US08846762B2

Reaction notes

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