1,2-Ethanediamine, N1,N1-bis(1-methylethyl)- → 4-(2-Diisopropylaminoethylamino)benzenesulfonic 2-(cyclopropanecarbonylamino)benzothiazol-6-yl ester

HRID 1867963Notes

Reaction equation

HRID 1867963 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]([N:30]([CH:34]([CH3:36])[CH3:35])[CH2:31][CH2:32][NH2:33])([CH3:29])[CH3:28]>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:33][CH2:32][CH2:31][N:30]([CH:34]([CH3:36])[CH3:35])[CH:27]([CH3:29])[CH3:28])=[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 84591,2-Ethanediamine, N1,N1-bis(1-methylethyl)-HCID 115239994-Fluorobenzenesulfonic acid 2-(cyclopropanecarbonylamino)-benzothiazol-6-yl ester

Product 1

HCID 116849754-(2-Diisopropylaminoethylamino)benzenesulfonic 2-(cyclopropanecarbonylamino)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) (100 mg, 255 μmol) and N,N-diisopropyl-ethane-1,2-diamine (147 mg, 1.02 mmol) in 2 ml of NMP is heated at 110° C. by microwave for 10 minutes. The crude reaction product is purified by preparative LC/MS (basic medium (pH 9)) to give after freeze-drying 66 mg of 4-(2-hydroxy-2-methylpropylamino)benzenesulfonic 2-(cyclopropanecarbonyl-amino)benzothiazol-6-yl ester (beige-colored 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 66 mg of 4-(2-hydroxy-2-methylpropylamino)benzenesulfonic 2-(cyclopropanecarbonyl-amino)benzothiazol-6-yl ester (beige-colored solid)

Sources & evidence

ORD record
ord-7812bb8b14454e31bb4e2ede62cb3923
Source dataset
uspto-grants-2009_12
Patent number
US07632952B2

Reaction notes

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