4-(4-(Pyridin-3-yl)-1H-imidazol-1-yl)butan-1-amine → 4-[4-(4-Pyrid-3-ylimidazol-1-yl)butylamino]-benzenesulfonic 2-(cyclopropanecarbonylamino)benzothiazol-6-yl ester

HRID 1867964Notes

Reaction equation

HRID 1867964 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[CH:32]=[CH:31][CH:30]=[C:29]([C:33]2[N:34]=[CH:35][N:36]([CH2:38][CH2:39][CH2:40][CH2:41][NH2:42])[CH:37]=2)[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:42][CH2:41][CH2:40][CH2:39][CH2:38][N:36]5[CH:37]=[C:33]([C:29]6[CH:28]=[N:27][CH:32]=[CH:31][CH:30]=6)[N:34]=[CH:35]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 110421604-(4-(Pyridin-3-yl)-1H-imidazol-1-yl)butan-1-amineHCID 115239994-Fluorobenzenesulfonic acid 2-(cyclopropanecarbonylamino)-benzothiazol-6-yl ester

Product 1

HCID 115416084-[4-(4-Pyrid-3-ylimidazol-1-yl)butylamino]-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) (50 mg, 127.4 μmol) and 4-(4-pyrid-3-ylimidazol-1-yl)butylamine (110.2 mg, 0.51 mmol) in 0.5 ml of NMP is heated at 150° C. by microwave for 8 minutes. The crude reaction product is purified by preparative LC/MS (basic medium (pH 9)) to give after freeze-drying 36 mg of 4-(2-hydroxy-2-methylpropylamino)benzenesulfonic 2-(cyclo-propanecarbonylamino)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 36 mg of 4-(2-hydroxy-2-methylpropylamino)benzenesulfonic 2-(cyclo-propanecarbonylamino)benzothiazol-6-yl ester (beige-colored solid)

Sources & evidence

ORD record
ord-addae98b79d54e2e9731d9f40046de6f
Source dataset
uspto-grants-2009_12
Patent number
US07632952B2

Reaction notes

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