Chlorotrimethylsilane → 4-(4-(1-methyl-1H-indazol-5-ylamino)-7-tosyl-7H-pyrrolo[2,3-d]pyrimidin-2-ylamino)benzamide

HRID 645714Notes

Reaction equation

HRID 645714 reaction equation
Cl[C:2]1[N:3]=[C:4]([NH:21][C:22]2[CH:23]=[C:24]3[C:28](=[CH:29][CH:30]=2)[N:27]([CH3:31])[N:26]=[CH:25]3)[C:5]2[CH:10]=[CH:9][N:8]([S:11]([C:14]3[CH:20]=[CH:19][C:17]([CH3:18])=[CH:16][CH:15]=3)(=[O:13])=[O:12])[C:6]=2[N:7]=1.[NH2:32][C:33]1[CH:41]=[CH:40][C:36]([C:37]([NH2:39])=[O:38])=[CH:35][CH:34]=1.C[Si](Cl)(C)C>C(O)CCC>[CH3:31][N:27]1[C:28]2[C:24](=[CH:23][C:22]([NH:21][C:4]3[C:5]4[CH:10]=[CH:9][N:8]([S:11]([C:14]5[CH:20]=[CH:19][C:17]([CH3:18])=[CH:16][CH:15]=5)(=[O:13])=[O:12])[C:6]=4[N:7]=[C:2]([NH:32][C:33]4[CH:41]=[CH:40][C:36]([C:37]([NH2:39])=[O:38])=[CH:35][CH:34]=4)[N:3]=3)=[CH:30][CH:29]=2)[CH:25]=[N:26]1

Participants

5

Reactant 3

HCID 6397ChlorotrimethylsilaneHCID 760794-AminobenzamideHCID 866280432-chloro-N-(1-methyl-1H-indazol-5-yl)-7-tosyl-7H-pyrrolo[2,3-d]pyrimidin-4-amine

Product 1

HCID 685816284-(4-(1-methyl-1H-indazol-5-ylamino)-7-tosyl-7H-pyrrolo[2,3-d]pyrimidin-2-ylamino)benzamideYield 20.7%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent2×

Procedure

A mixture of 2-chloro-N-(1-methyl-1H-indazol-5-yl)-7-tosyl-7H-pyrrolo[2,3-d]pyrimidin-4-amine (158 mg, 0.349 mmol), 4-aminobenzamide (100 mg, 0.735 mmol) and TMSCl (0.300 mL, 2.37 mmol) in nBuOH (3 mL) was stirred at 135° C. for 20 h. nBuOH was removed in vacuo. The residue was purified by HPLC to give 4-(4-(1-methyl-1H-indazol-5-ylamino)-7-tosyl-7H-pyrrolo[2,3-d]pyrimidin-2-ylamino)benzamide (40 mg).

Workup

  1. customwas removed in vacuo
  2. customThe residue was purified by HPLC

Sources & evidence

ORD record
ord-f6e5cad3a0ef4d36949c6141aea655d4
Source dataset
uspto-grants-2010_04
Patent number
US07705004B2

Reaction notes

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