1H-Imidazole-1-propanamine → 4-(3-Imidazol-1-ylpropylamino)benzenesulfonic 2-(cyclopropanecarbonylamino)benzothiazol-6-yl ester

HRID 1867960Notes

Reaction equation

HRID 1867960 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.[N:27]1([CH2:32][CH2:33][CH2:34][NH2:35])[CH:31]=[CH:30][N:29]=[CH: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:35][CH2:34][CH2:33][CH2:32][N:27]5[CH:31]=[CH:30][N:29]=[CH: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 787361H-Imidazole-1-propanamineHCID 115239994-Fluorobenzenesulfonic acid 2-(cyclopropanecarbonylamino)-benzothiazol-6-yl ester

Product 1

HCID 116274094-(3-Imidazol-1-ylpropylamino)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, 0.255 mmol) and 3-imidazol-1-yl-propylamine (123 μl, 1.019 mmol) in 2 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 63 mg of 4-(3-imidazol-1-ylpropylamino)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 63 mg of 4-(3-imidazol-1-ylpropylamino)benzenesulfonic 2-(cyclopropanecarbonylamino)benzothiazol-6-yl ester (white solid)

Sources & evidence

ORD record
ord-1bd95ef9519145578aa982ae2c34c1b6
Source dataset
uspto-grants-2009_12
Patent number
US07632952B2

Reaction notes

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