Acetic Anhydride → HCID 57377453, compound

HRID 332185Notes

Reaction equation

HRID 332185 reaction equation
[NH2:1][CH2:2][CH2:3][S:4]([C:7]1[CH:12]=[CH:11][C:10]([Cl:13])=[CH:9][C:8]=1[NH:14][S:15]([C:18]1[CH:23]=[CH:22][C:21]([Cl:24])=[C:20]([C:25]([F:28])([F:27])[F:26])[CH:19]=1)(=[O:17])=[O:16])(=[O:6])=[O:5].CCN(CC)CC.[C:36](OC(=O)C)(=[O:38])[CH3:37]>C(Cl)Cl.CN(C1C=CN=CC=1)C>[Cl:13][C:10]1[CH:11]=[CH:12][C:7]([S:4]([CH2:3][CH2:2][NH:1][C:36](=[O:38])[CH3:37])(=[O:5])=[O:6])=[C:8]([NH:14][S:15]([C:18]2[CH:23]=[CH:22][C:21]([Cl:24])=[C:20]([C:25]([F:26])([F:27])[F:28])[CH:19]=2)(=[O:17])=[O:16])[CH:9]=1

Participants

6

Reactant 3

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 67972284HCID 67972284, compound

Product 1

HCID 57377453HCID 57377453, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of N-{2-[(2-aminoethyl)sulfonyl]-5-chlorophenyl}-4-chloro-3-(trifluoromethyl)benzenesulfonamide (23 mg, 0.048 mmol) in CH2Cl2 (2 ml) was added Et3N (14 μl, 0.10 mmol), acetic anhydride (5 μl, 0.053 mmol), and catalytic amount of DMAP. The reaction was stirred at room temperature for 1 h and was concentrated. The crude product was purified by column chromatography on silica gel (0→10% MeOH in ethyl acetate), followed by PTLC (10% MeOH in ethyl acetate) to give the title compound.

Workup

  1. concentrationwas concentrated
  2. customThe crude product was purified by column chromatography on silica gel (0→10% MeOH in ethyl acetate)

Sources & evidence

ORD record
ord-78c31520e9504d9a9be9e552b18c29fd
Source dataset
uspto-grants-2014_11
Patent number
US08877804B2

Reaction notes

Loading…