Pyridine → 5-Pyridin-2-ylthiophene-2-sulfonic acid 2-(cyclopropanecarbonyl-amino)benzothiazol-6-yl ester

HRID 1867998Notes

Reaction equation

HRID 1867998 reaction equation
[OH:1][C:2]1[CH:16]=[CH:15][C:5]2[N:6]=[C:7]([NH:9][C:10]([CH:12]3[CH2:14][CH2:13]3)=[O:11])[S:8][C:4]=2[CH:3]=1.N1C=CC=CC=1.[N:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1[C:29]1[S:33][C:32]([S:34](Cl)(=[O:36])=[O:35])=[CH:31][CH:30]=1>CN(C)C1C=CN=CC=1.CC(C)=O>[CH:12]1([C:10]([NH:9][C:7]2[S:8][C:4]3[CH:3]=[C:2]([O:1][S:34]([C:32]4[S:33][C:29]([C:24]5[CH:25]=[CH:26][CH:27]=[CH:28][N:23]=5)=[CH:30][CH:31]=4)(=[O:35])=[O:36])[CH:16]=[CH:15][C:5]=3[N:6]=2)=[O:11])[CH2:13][CH2:14]1

Participants

6

Reactant 3

HCID 1049PyridineHCID 27372315-(2-Pyridyl)thiophene-2-sulfonyl chlorideHCID 57980821N-(6-hydroxy-1,3-benzothiazol-2-yl)cyclopropanecarboxamide2×

Product 1

HCID 579808415-Pyridin-2-ylthiophene-2-sulfonic acid 2-(cyclopropanecarbonyl-amino)benzothiazol-6-yl esterYield 8.5%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 180AcetoneSolvent

Procedure

A solution of cyclopropanecarboxylic acid (6-hydroxybenzothiazol-2-yl)amide (intermediate 6) (60 mg, 0.256 mmol), pyridine (80 μl, 0.991 mmol), 4-dimethylaminopyridine (3 mg, 0.025 mmol) and 5-(2-pyridyl)thiophene-2-sulfonyl chloride (99 mg, 0.384 mmol) in 2 ml of acetone is stirred for 24 hours at 40° C. The reaction medium is concentrated to dryness, taken up in 2 ml of DMSO and purified 4 times by preparative LC/MS (method B) to give 10 mg of 5-pyridin-2-ylthiophene-2-sulfonic acid 2-(cyclopropanecarbonyl-amino)benzothiazol-6-yl ester.

Workup

  1. concentrationThe reaction medium is concentrated to dryness
  2. custompurified 4 times by preparative LC/MS (method B)

Sources & evidence

ORD record
ord-d09f54cec603445fbb7c43e011f387b2
Source dataset
uspto-grants-2009_12
Patent number
US07632952B2

Reaction notes

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