Methanol → Carbon Dioxide

HRID 1177639Notes

Reaction equation

HRID 1177639 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([NH:26][CH:27]2[CH2:30][CH:29]([C:31]([OH:33])=[O:32])[CH2:28]2)[CH:5]=[CH:6][C:7]=1[C:8]1[S:9][C:10]2[C:15]([N:16]=1)=[CH:14][CH:13]=[C:12]([C:17]1([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[CH2:19][CH2:18]1)[N:11]=2.S(Cl)(Cl)=O.[CH3:38]O>>[C:31](=[O:33])=[O:32].[F:1][C:2]1[CH:3]=[C:4]([NH:26][C@@H:27]2[CH2:30][C@H:29]([C:31]([O:33][CH3:38])=[O:32])[CH2:28]2)[CH:5]=[CH:6][C:7]=1[C:8]1[S:9][C:10]2[C:15]([N:16]=1)=[CH:14][CH:13]=[C:12]([C:17]1([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[CH2:18][CH2:19]1)[N:11]=2

Participants

5

Reactant 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 591748373-(3-Fluoro-4-(5-(1-phenylcyclopropyl)thiazolo[5,4-b]pyridin-2-yl)-phenylamino)-cyclobutanecarboxylic acid

Product 2

HCID 280Carbon DioxideYield 12%HCID 178501321HCID 178501321, compound

Procedure

To 3-(3-fluoro-4-(5-(1-phenylcyclopropyl)thiazolo[5,4-b]pyridin-2-yl)-phenylamino)-cyclobutanecarboxylic acid (230 mg, 0.501 mmol) was added methanol (5.0 mL) and thionyl chloride (37 μl, 0.501 mmol) before it was stirred at ambient temperature for 30 min; the reaction mixture was concentrated, and the diastereomers were separated via SFC (Column: ChiralPak AS-H, Mobile Phase: liquid CO2/20% MeOH with diethylamine; then Column: Princeton Pyridine, Mobile Phase: liquid CO2/12% MeOH) to give methyl cis-3-((3-fluoro-4-(5-(1-phenyl-cyclopropyl)[1,3]thiazolo[5,4-b]pyridin-2-yl)phenyl)amino)-cyclobutanecarboxylate. MS (ESI) m/z: Calculated: 473.2; Observed: 474.1 (M++H).

Workup

  1. concentrationthe reaction mixture was concentrated
  2. customthe diastereomers were separated via SFC (Column

Sources & evidence

ORD record
ord-ec3008e2d40b4a688d27e659043e21d4
Source dataset
uspto-grants-2010_11
Patent number
US07842685B2

Reaction notes

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