Chlorotrimethylsilane → 1-(4-(4-(4-(1H-indazol-6-ylamino)-5-methyl-7-tosyl-7H-pyrrolo[2,3-d]pyrimidin-2-ylamino)phenyl)piperazin-1-yl)ethanone

HRID 645706Notes

Reaction equation

Cl[C:2]1[N:3]=[C:4]([NH:23][C:24]2[CH:32]=[C:31]3[C:27]([CH:28]=[N:29][NH:30]3)=[CH:26][CH:25]=2)[C:5]2[C:10]([CH2:11]C)=[CH:9][N:8]([S:13]([C:16]3[CH:22]=[CH:21][C:19]([CH3:20])=[CH:18][CH:17]=3)(=[O:15])=[O:14])[C:6]=2[N:7]=1.[NH2:33][C:34]1[CH:39]=[CH:38][C:37]([N:40]2[CH2:45][CH2:44][N:43]([C:46](=[O:48])[CH3:47])[CH2:42][CH2:41]2)=[CH:36][CH:35]=1.C[Si](Cl)(C)C>C(O)CCC>[NH:30]1[C:31]2[C:27](=[CH:26][CH:25]=[C:24]([NH:23][C:4]3[C:5]4[C:10]([CH3:11])=[CH:9][N:8]([S:13]([C:16]5[CH:17]=[CH:18][C:19]([CH3:20])=[CH:21][CH:22]=5)(=[O:15])=[O:14])[C:6]=4[N:7]=[C:2]([NH:33][C:34]4[CH:35]=[CH:36][C:37]([N:40]5[CH2:41][CH2:42][N:43]([C:46](=[O:48])[CH3:47])[CH2:44][CH2:45]5)=[CH:38][CH:39]=4)[N:3]=3)[CH:32]=2)[CH:28]=[N:29]1

Participants

Conditions

Temperature: 115 °C

Procedure

To a mixture of 2-Chloro-N-(1H-indazol-6-yl)-5-ethyl-7-tosyl-7H-pyrrolo[2,3-d]pyrimidin-4-amine (0.08 g, 0.17 mmol) and 1-(4-(4-aminophenyl)piperazin-1-yl)ethanone (0.075 g, 0.34 mmol) in n-butyl alcohol (2 mL) was added TMSCl (0.011 mL, 0.086 mmol). After heating at 115° C. for 48 h, the mixture was purified by preparative HPLC to give 1-(4-(4-(4-(1H-indazol-6-ylamino)-5-methyl-7-tosyl-7H-pyrrolo[2,3-d]pyrimidin-2-ylamino)phenyl)piperazin-1-yl)ethanone (0.02 g).

Workup

customthe mixture was purified by preparative HPLC

Sources & evidence

ORD record: ord-4c3746704ab44651ab115c985778afd6
Source dataset: uspto-grants-2010_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07705004B2

Reaction notes

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