Acetic Anhydride → HCID 57377453, compound

HRID 2097746Notes

Reaction equation

HRID 2097746 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-a83192caf53949da918d5c7a10f02b4a
Source dataset
uspto-grants-2013_05
Patent number
US08450367B2

Reaction notes

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