Cyclopentylamine → 4-Cyclopentylaminobenzenesulfonic 2-(cyclo-propanecarbonylamino)benzothiazol-6-yl ester

HRID 1867959Notes

Reaction equation

HRID 1867959 reaction equation
[CH:1]1([C:4]([NH:6][C:7]2[S:8][C:9]3[CH:15]=[C:14]([O:16][S:17]([C:20]4[CH:25]=[CH:24][C:23](F)=[CH:22][CH:21]=4)(=[O:19])=[O:18])[CH:13]=[CH:12][C:10]=3[N:11]=2)=[O:5])[CH2:3][CH2:2]1.[CH:27]1([NH2:32])[CH2:31][CH2:30][CH2:29][CH2:28]1>CN1C(=O)CCC1>[CH:1]1([C:4]([NH:6][C:7]2[S:8][C:9]3[CH:15]=[C:14]([O:16][S:17]([C:20]4[CH:25]=[CH:24][C:23]([NH:32][CH:27]5[CH2:31][CH2:30][CH2:29][CH2:28]5)=[CH:22][CH:21]=4)(=[O:19])=[O:18])[CH:13]=[CH:12][C:10]=3[N:11]=2)=[O:5])[CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 2906CyclopentylamineHCID 115239994-Fluorobenzenesulfonic acid 2-(cyclopropanecarbonylamino)-benzothiazol-6-yl ester

Product 1

HCID 116049574-Cyclopentylaminobenzenesulfonic 2-(cyclo-propanecarbonylamino)benzothiazol-6-yl ester

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

A solution of 4-fluorobenzenesulfonic 2-(cyclopropanecarbonylamino)benzo-thiazol-6-yl ester (example 7) (50 mg, 127.4 μmol) and cyclopentylamine (51 μl, 0.51 mmol) in 0.5 ml of NMP is heated at 150° C. by microwave for 5 minutes. The crude reaction product is purified by preparative LC/MS (basic medium (pH 9)) to give after freeze-drying 38 mg of 4-cyclopentylamino-benzenesulfonic 2-(cyclopropanecarbonylamino)benzothiazol-6-yl ester (white solid).

Workup

  1. customThe crude reaction product
  2. customis purified by preparative LC/MS (basic medium (pH 9))
  3. customto give
  4. dry with materialafter freeze-drying 38 mg of 4-cyclopentylamino-benzenesulfonic 2-(cyclopropanecarbonylamino)benzothiazol-6-yl ester (white solid)

Sources & evidence

ORD record
ord-f967e4eb8bcd43c8a7e6cf2c522e8f3d
Source dataset
uspto-grants-2009_12
Patent number
US07632952B2

Reaction notes

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