Water → HCID 59135855, compound

HRID 1960461Notes

Reaction equation

HRID 1960461 reaction equation
[NH2:1][CH2:2][CH:3]1[S:7][C:6]([C:8]2[NH:9][C:10]3[C:15]([CH:16]=2)=[CH:14][CH:13]=[CH:12][C:11]=3[N:17]([CH3:26])[S:18]([C:21]2[S:22][CH:23]=[CH:24][CH:25]=2)(=[O:20])=[O:19])=[N:5][CH2:4]1.[C:27](OC(=O)C)(=[O:29])[CH3:28].O>CN(C)C(=O)C>[CH3:26][N:17]([S:18]([C:21]1[S:22][CH:23]=[CH:24][CH:25]=1)(=[O:20])=[O:19])[C:11]1[CH:12]=[CH:13][CH:14]=[C:15]2[C:10]=1[NH:9][C:8]([C:6]1[S:7][CH:3]([CH2:2][NH:1][C:27](=[O:29])[CH3:28])[CH2:4][N:5]=1)=[CH:16]2

Participants

5

Reactant 3

HCID 962WaterHCID 7918Acetic AnhydrideHCID 57503214HCID 57503214, compound

Product 1

HCID 59135855HCID 59135855, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

To a solution of N-{2-[5-(aminomethyl)-4,5-dihydro-1,3-thiazol-2-yl]-1H-indol-7-yl}-N-methylthiophene-2-sulfonamide (0.27 g) in N,N-dimethylacetamide (6 mL) was added acetic anhydride (0.10 mL) at 0° C., and the, mixture was stirred for 30 min. Water was added to the reaction mixture, and the precipitated solid was collected by filtration, washed with water, and dried. The obtained solid was subjected to silica gel column chromatography to give the title compound. (0.20 g, yield 68%) as pale-yellow crystals from a fraction eluted with ethyl acetate-hexane (95:5, volume ratio). melting point 212-213° C.

Workup

  1. filtrationthe precipitated solid was collected by filtration
  2. washwashed with water
  3. customdried

Sources & evidence

ORD record
ord-e17a14109bcc4cb496c47bc4ee5798e5
Source dataset
uspto-grants-2013_04
Patent number
US08410087B2

Reaction notes

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