Dimethylformamide → N-{6-[4-(4-Methylpiperazin-1-yl)pyrimidin-2-ylamino]benzothiazol-2-yl}benzamide

HRID 2102823Notes

Reaction equation

HRID 2102823 reaction equation
[NH2:1][C:2]1[CH:19]=[CH:18][C:5]2[N:6]=[C:7]([NH:9][C:10](=[O:17])[C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)[S:8][C:4]=2[CH:3]=1.Cl[C:21]1[N:26]=[C:25]([N:27]2[CH2:32][CH2:31][N:30]([CH3:33])[CH2:29][CH2:28]2)[CH:24]=[CH:23][N:22]=1.CN(C)C=O.ClCCl>C(O)C.CO>[CH3:33][N:30]1[CH2:29][CH2:28][N:27]([C:25]2[CH:24]=[CH:23][N:22]=[C:21]([NH:1][C:2]3[CH:19]=[CH:18][C:5]4[N:6]=[C:7]([NH:9][C:10](=[O:17])[C:11]5[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=5)[S:8][C:4]=4[CH:3]=3)[N:26]=2)[CH2:32][CH2:31]1

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 6344DichloromethaneHCID 810331N-(6-amino-1,3-benzothiazol-2-yl)benzamideHCID 17142252-Chloro-4-(4-methylpiperazin-1-yl)pyrimidine

Product 1

HCID 23132480N-{6-[4-(4-Methylpiperazin-1-yl)pyrimidin-2-ylamino]benzothiazol-2-yl}benzamide

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 887MethanolSolvent

Procedure

N-{6-[4-(4-Methylpiperazin-1-yl)pyrimidin-2-ylamino]benzothiazol-2-yl}benzamide was prepared by heating a mixture of N-(6-aminobenzothiazol-2-yl)benzamide (IM 2, 50 mg, 0.186 mmol) and 2-chloro-4-(4methylpiperazin1-yl)pyrimidine (IM 10, 40 mg, 0.186 mmol) in ethanol (3 mL) to 80° C. for 4 days. After dissolving the precipitate by addition of dimethylformamide, pTLC (dichloromethane:methanol=4.1) yielded a solid (44 mg, 0.100 mmol, 54%). LC/ESI-MS: m/z=446 [M+H]+; m/z=444 [M−H]−; Rt=2.12 min.

Workup

  1. temperatureby heating
  2. dissolutionAfter dissolving the precipitate

Sources & evidence

ORD record
ord-59a2a14b3c344cafb1c03889e0e253c4
Source dataset
uspto-grants-2009_08
Patent number
US07576090B2

Reaction notes

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