Methanol → HCID 135719064, compound

HRID 1814143Notes

Reaction equation

HRID 1814143 reaction equation
C(O[C:4](=[O:30])[CH:5]([F:29])[C:6]([C:8]1[N:20]([CH2:21][C:22]2[CH:27]=[CH:26][C:25]([F:28])=[CH:24][CH:23]=2)[C:11]2=[N:12][CH:13]=[C:14]([S:16]([CH3:19])(=[O:18])=[O:17])[CH:15]=[C:10]2[CH:9]=1)=O)C.C(O)(=O)C.[CH:35]([NH2:37])=[NH:36].CO.C[O-].[Na+]>C(OCC)(=O)C.C(O)(=O)C>[F:29][C:5]1[C:4](=[O:30])[NH:37][CH:35]=[N:36][C:6]=1[C:8]1[N:20]([CH2:21][C:22]2[CH:27]=[CH:26][C:25]([F:28])=[CH:24][CH:23]=2)[C:11]2=[N:12][CH:13]=[C:14]([S:16]([CH3:19])(=[O:18])=[O:17])[CH:15]=[C:10]2[CH:9]=1

Participants

7

Reactant 4

HCID 887MethanolHCID 160693Formamidine acetateHCID 10942334Sodium MethoxideHCID 86591733HCID 86591733, compound

Product 1

HCID 135719064HCID 135719064, compoundYield 27.4%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of 2-fluoro-3-(1-(4-fluorobenzyl)-5-methanesulfonyl-1H-pyrrolo[2,3-b]pyridin-2-yl)-3-oxopropionic acid ethyl ester obtained in Example 36 (3) (88 mg), formamidine acetate (42 mg) and methanol (1.2 ml), sodium methoxide (0.6 ml, 1 mol/l solution in methanol) was added at 15 to 30° C. and the mixture was stirred at the same temperature for 18 hours. The mixture was neutralized with acetic acid and diluted with ethyl acetate. The organic layer was washed with water, dried and concentrated under reduced pressure. The resulting residue was separated using silica gel column chromatography (methanol:dichloromethane=5:95) to obtain the desired product (23 mg) in a white amorphous form.

Workup

  1. additionwas added at 15 to 30° C.
  2. washThe organic layer was washed with water
  3. customdried
  4. concentrationconcentrated under reduced pressure
  5. customThe resulting residue was separated

Sources & evidence

ORD record
ord-c72733b1e4e64ecc9f39d73daeb3b9d0
Source dataset
uspto-grants-2005_04
Patent number
US06875770B2

Reaction notes

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