Chlorotrimethylsilane → HCID 86636622, compound

HRID 2281476Notes

Reaction equation

HRID 2281476 reaction equation
Cl[C:2]1[N:3]=[C:4]([NH:11][C:12]2[CH:13]=[C:14]([CH:21]=[CH:22][CH:23]=2)[O:15][CH2:16][C:17]([NH:19][CH3:20])=[O:18])[C:5]2[CH:10]=[CH:9][NH:8][C:6]=2[N:7]=1.[NH2:24][C:25]1[CH:33]=[C:32]2[C:28]([CH:29]=[N:30][NH:31]2)=[CH:27][CH:26]=1.C[Si](Cl)(C)C>C(O)CCC>[NH:31]1[C:32]2[C:28](=[CH:27][CH:26]=[C:25]([NH:24][C:2]3[N:3]=[C:4]([NH:11][C:12]4[CH:13]=[C:14]([CH:21]=[CH:22][CH:23]=4)[O:15][CH2:16][C:17]([NH:19][CH3:20])=[O:18])[C:5]4[CH:10]=[CH:9][NH:8][C:6]=4[N:7]=3)[CH:33]=2)[CH:29]=[N:30]1

Participants

5

Reactant 3

HCID 6397ChlorotrimethylsilaneHCID 814231H-Indazol-6-amineHCID 86636621HCID 86636621, compound

Product 1

HCID 86636622HCID 86636622, compoundYield 8.7%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Conditions

Temperature
115 °C

Procedure

To a mixture of 2-(3-(2-chloro-7H-pyrrolo[2,3-d]pyrimidin-4-ylamino)phenoxy-N-methylacetamide (0.062 g) in nBuOH (0.6 mL) was added 6-aminoindazole (0.028 g) and TMSCl (0.013 mL). After heating at 115° C. for 15 h, the mixture was purified by prep HPLC to give 2-(3-(2-(1H-indazol-6-ylamino)-7H-pyrrolo[2,3-d]pyrimidin-4-ylamino)phenoxy-N-methylacetamide (0.007 g, MS calcd for C22H20N8O2 428.4. found [MH] 429.1; UV 238.1, 311.6 nm).

Workup

  1. customthe mixture was purified by prep HPLC

Sources & evidence

ORD record
ord-2d9cd8c593444415af7e5e72d3589a53
Source dataset
uspto-grants-2015_09
Patent number
US09139581B2

Reaction notes

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