N-(6-amino-1,3-benzothiazol-2-yl)benzamide → N-{6-[4-(5-Methylpyrazol-3-ylamino)pyrimidin-2-ylamino]benzothiazol-2-yl)benzamide

HRID 2102824Notes

Reaction equation

HRID 2102824 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]([NH:27][C:28]2[CH:32]=[C:31]([CH3:33])[NH:30][N:29]=2)[CH:24]=[CH:23][N:22]=1>C(O)C>[CH3:33][C:31]1[NH:30][N:29]=[C:28]([NH: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)[CH:32]=1

Participants

4

Reactant 2

HCID 810331N-(6-amino-1,3-benzothiazol-2-yl)benzamideHCID 231324822-Chloro-N-(5-methyl-1H-pyrazol-3-yl)pyrimidin-4-amine

Product 1

HCID 23132472N-{6-[4-(5-Methylpyrazol-3-ylamino)pyrimidin-2-ylamino]benzothiazol-2-yl)benzamide

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

N-{6-[4-(5-Methylpyrazol-3-ylamino)pyrimidin-2-ylamino]benzothiazol-2-yl}benzamide was prepared by heating a mixture of N-(6-aminobenzothiazol-2-yl)benzamide (IM 2, 35 mg, 0.13 mmol) and (2-chloropyrimidin-4-yl)-(5-methylpyrazol-3-yl)amine (IM 11, 30 mg, 0.143 mmol) in ethanol (3 mL) to 80° C. for 9 h. The precipitate was separated by filtration, washed with ethanol and dried (38 mg, 85 μmol, 66%). LC/ESI-MS: m/z=443 [M+H]+; m/z =441 [M−H]−; Rt=2.80 min.

Workup

  1. temperatureby heating
  2. customThe precipitate was separated by filtration
  3. washwashed with ethanol
  4. customdried (38 mg, 85 μmol, 66%)

Sources & evidence

ORD record
ord-d4aea8b652c247d3bcf1d1e33db9378b
Source dataset
uspto-grants-2009_08
Patent number
US07576090B2

Reaction notes

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