Sodium Methoxide → HCID 67288679, compound

HRID 527061Notes

Reaction equation

HRID 527061 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:10]([C:11]3[N:16]=[C:15]([NH:17][CH:18]4[CH2:23][CH2:22][CH2:21][CH:20]([C:24]([NH:26][CH2:27][CH3:28])=[O:25])[CH:19]4[OH:29])[C:14]([F:30])=[CH:13][N:12]=3)=[CH:9][N:8](S(C3C=CC(C)=CC=3)(=O)=O)[C:5]2=[N:6][CH:7]=1.C[O-].[Na+]>CO>[Cl:1][C:2]1[CH:3]=[C:4]2[C:10]([C:11]3[N:16]=[C:15]([NH:17][CH:18]4[CH2:23][CH2:22][CH2:21][CH:20]([C:24]([NH:26][CH2:27][CH3:28])=[O:25])[CH:19]4[OH:29])[C:14]([F:30])=[CH:13][N:12]=3)=[CH:9][NH:8][C:5]2=[N:6][CH:7]=1

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 686407093-[[2-[5-chloro-1-(p-tolylsulfonyl)pyrrolo[2,3-b]pyridin-3-yl]-5-fluoro-pyrimidin-4-yl]amino]-N-ethyl-2-hydroxy-cyclohexanecarboxamide2×

Product 1

HCID 67288679HCID 67288679, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

3-[[2-[5-chloro-1-(p-tolylsulfonyl)pyrrolo[2,3-b]pyridin-3-yl]-5-fluoro-pyrimidin-4-yl]amino]-N-ethyl-2-hydroxy-cyclohexanecarboxamide, 65c, was treated with NaOMe in MeOH. The product was purified by preparatory HPLC to provide 3-[[2-(5-chloro-1H-pyrrolo[2,3-b]pyridin-3-yl)-5-fluoro-pyrimidin-4-yl]amino]-N-ethyl-2-hydroxy-cyclohexanecarboxamide as a mixture of stereoisomers. LCMS: 433.35 (M+1).

Workup

  1. customThe product was purified by preparatory HPLC

Sources & evidence

ORD record
ord-5aca1cc0bd094b5888515880925770f0
Source dataset
uspto-grants-2016_05
Patent number
US09345708B2

Reaction notes

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