Chlorotrimethylsilane → HCID 57990337, compound

HRID 2381670Notes

Reaction equation

HRID 2381670 reaction equation
Cl[C:2]1[N:3]=[C:4]([NH:11][CH:12]2[CH2:17][CH2:16][CH2:15][CH2:14][CH:13]2[NH2:18])[C:5]2[CH:10]=[CH:9][NH:8][C:6]=2[N:7]=1.[NH2:19][C:20]1[CH:25]=[CH:24][C:23]([N:26]([CH3:30])[C:27](=[O:29])[CH3:28])=[CH:22][CH:21]=1.C[Si](Cl)(C)C>C(O)CCC>[NH2:18][CH:13]1[CH2:14][CH2:15][CH2:16][CH2:17][CH:12]1[NH:11][C:4]1[C:5]2[CH:10]=[CH:9][NH:8][C:6]=2[N:7]=[C:2]([NH:19][C:20]2[CH:21]=[CH:22][C:23]([N:26]([CH3:30])[C:27](=[O:29])[CH3:28])=[CH:24][CH:25]=2)[N:3]=1

Participants

5

Reactant 3

HCID 6397ChlorotrimethylsilaneHCID 67068N-(4-Aminophenyl)-N-methylacetamideHCID 86636618HCID 86636618, compound

Product 1

HCID 57990337HCID 57990337, compoundYield 9%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Conditions

Temperature
116 °C

Procedure

A mixture of N1-(2-chloro-7H-pyrrolo[2,3-d]pyrimidin-4-yl)cyclohexane-1,2-diamine (44 mg, 0.17 mmol), N-(4-aminophenyl)-N-methylacetamide (56 mg, 0.34 mmol) and trimethylsilyl chloride (0.146 mL, 1.15 mmol) in nBuOH (2 mL) was heated at 116° C. for 4 h. It was then purified by HPLC to give the titled compound (6 mg). MS 394.2 (M+H); UV 201.4, 262.7, 306.7 nm.

Workup

  1. customIt was then purified by HPLC

Sources & evidence

ORD record
ord-8387d401ed7b48e080e3379f60f4f4dd
Source dataset
uspto-grants-2012_09
Patent number
US08258144B2

Reaction notes

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