Triethylamine → Thiophene-2-sulfonic acid {3-[5-(2-methyl-benzoyl)-thiazol-2-ylamino]-propyl}-amide

HRID 2119591Notes

Reaction equation

HRID 2119591 reaction equation
Cl.[NH2:2][CH2:3][CH2:4][CH2:5][NH:6][C:7]1[S:8][C:9]([C:12]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[CH3:20])=[O:13])=[CH:10][N:11]=1.[S:21]1[CH:25]=[CH:24][CH:23]=[C:22]1[S:26](Cl)(=[O:28])=[O:27].CCN(CC)CC>CO.C(Cl)Cl>[CH3:20][C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=1[C:12]([C:9]1[S:8][C:7]([NH:6][CH2:5][CH2:4][CH2:3][NH:2][S:26]([C:22]2[S:21][CH:25]=[CH:24][CH:23]=2)(=[O:28])=[O:27])=[N:11][CH:10]=1)=[O:13]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 855182-Thiophenesulfonyl chlorideHCID 23442547[2-(3-Amino-propylamino)-thiazol-5-yl]-o-tolyl-methanone hydrochloride

Product 1

HCID 20616896Thiophene-2-sulfonic acid {3-[5-(2-methyl-benzoyl)-thiazol-2-ylamino]-propyl}-amideYield 27%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of 31.1 mg (0.1 mmol) [2-(3-Amino-propylamino)-thiazol-5-yl]-o-tolyl-methanone hydrochloride in 1 ml methanol, 18.2 mg (0.1 mmol) Thiophene-2-sulfonyl chloride in 1 ml DCM and 0.15 ml NEt3 was stirred for 16 h at 50° C. After evaporation to dryness the residue was taken up in 1.5 ml MeOH/formic acid 1/1 and subjected to preparative HPLC separation on reversed phase eluting with an acetonitrile/water gradient. Evaporation of product fractions yielded 11.4 mg (27%) of the title compound.

Workup

  1. customAfter evaporation to dryness the residue
  2. customHPLC separation on reversed phase
  3. washeluting with an acetonitrile/water gradient
  4. customEvaporation of product fractions

Sources & evidence

ORD record
ord-1e22dc8dca2c45239a1cb86782fc1fbc
Source dataset
uspto-grants-2004_02
Patent number
US06686381B2

Reaction notes

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