Chlorotrimethylsilane → N-(4-(4-(3-(aminomethyl)phenylamino)-7-tosyl-7H-pyrrolo[2,3-d]pyrimidin-2-ylamino)phenyl)-N-methylacetamide

HRID 2281487Notes

Reaction equation

HRID 2281487 reaction equation
Cl[C:2]1[N:3]=[C:4]([NH:21][C:22]2[CH:23]=[C:24]([CH:34]=[CH:35][CH:36]=2)[CH2:25][NH:26]C(=O)OC(C)(C)C)[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.[NH2:37][C:38]1[CH:43]=[CH:42][C:41]([N:44]([CH3:48])[C:45](=[O:47])[CH3:46])=[CH:40][CH:39]=1.C[Si](Cl)(C)C>C(O)CCC>[NH2:26][CH2:25][C:24]1[CH:23]=[C:22]([NH:21][C:4]2[C:5]3[CH:10]=[CH:9][N:8]([S:11]([C:14]4[CH:15]=[CH:16][C:17]([CH3:18])=[CH:19][CH:20]=4)(=[O:13])=[O:12])[C:6]=3[N:7]=[C:2]([NH:37][C:38]3[CH:39]=[CH:40][C:41]([N:44]([CH3:48])[C:45](=[O:47])[CH3:46])=[CH:42][CH:43]=3)[N:3]=2)[CH:36]=[CH:35][CH:34]=1

Participants

5

Reactant 3

HCID 6397ChlorotrimethylsilaneHCID 67068N-(4-Aminophenyl)-N-methylacetamideHCID 57990287tert-butyl 3-(2-chloro-7-tosyl-7H-pyrrolo[2,3-d]pyrimidin-4-ylamino)benzylcarbamate

Product 1

HCID 57990342N-(4-(4-(3-(aminomethyl)phenylamino)-7-tosyl-7H-pyrrolo[2,3-d]pyrimidin-2-ylamino)phenyl)-N-methylacetamideYield 8.4%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

A solution of tert-butyl 3-(2-chloro-7-tosyl-7H-pyrrolo[2,3-d]pyrimidin-4-ylamino)benzylcarbamate (306 mg, 0.580 mmol), N-(4-aminophenyl)-N-methylacetamide (190 mg, 1.16 mmol) and trimethylsilyl chloride (0.100 mL, 0.791 mmol) in nBuOH (5 mL) was stirred at 116° C. for 20 h. The mixture was then purified by HPLC to give N-(4-(4-(3-(aminomethyl)phenylamino)-7-tosyl-7H-pyrrolo[2,3-d]pyrimidin-2-ylamino)phenyl)-N-methylacetamide (27 mg).

Workup

  1. customThe mixture was then purified by HPLC

Sources & evidence

ORD record
ord-86bff98e3a4146ee9412b4f70cdb2c55
Source dataset
uspto-grants-2015_09
Patent number
US09139581B2

Reaction notes

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