Dimethyl Sulfoxide → HCID 178525790, compound

HRID 1177483Notes

Reaction equation

HRID 1177483 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH2:26][CH:27]2[CH2:30][C:29](C(O)=O)([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.CS(C)=O>O>[F:1][C:2]1[CH:3]=[C:4]([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:21]=[CH:22][CH:23]=[CH:24][CH:25]=3)[CH2:18][CH2:19]1)[N:11]=2)[CH2:26][C@@H:27]1[CH2:30][C@H:29]([C:31]([OH:33])=[O:32])[CH2:28]1

Participants

4

Reactant 2

HCID 679Dimethyl SulfoxideHCID 44601274HCID 44601274, compound

Product 1

HCID 178525790HCID 178525790, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
160 °C

Procedure

3-((3-Fluoro-4-(5-(1-phenylcyclopropyl)thiazolo[5,4-b]pyridine-2-yl)phenyl)-methyl)cyclobutane-1,1-dicarboxylic acid (0.360 g, 0.716 mmol) treated with 4 mL DMSO, fitted with a water cooled reflux condenser, and heated to 160° C. After 4 h, the reaction mixture was cooled to rt. The reaction mixture was partitioned between water and EtOAc. The organic layer was washed with water once, satd NaCl once and the organics were dried over anhydrous sodium sulfate, filtered, and concentrated in vacuo to give a light yellow solid, as an approximately 2:1 mixture of isomers. Separation by SFC (Gradient with Chiralpak IC (21×250 mm, 5 micron), pure methanol with CO2 70 mL/min) gave (cis)-3-(3-fluoro-4-(5-(1-phenylcyclopropyl)-thiazolo[5,4-b]pyridine-2-yl)benzyl)cyclobutanecarboxylic acid as a white solid. MS (ESI) m/z: calculated: 458.2; Observed: 459.1 (M++1).

Workup

  1. temperaturecooled
  2. temperaturereflux condenser
  3. temperaturethe reaction mixture was cooled to rt
  4. customThe reaction mixture was partitioned between water and EtOAc
  5. washThe organic layer was washed with water once
  6. dry with materialthe organics were dried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customto give a light yellow solid
  10. additionas an approximately 2:1 mixture of isomers
  11. customSeparation by SFC (Gradient with Chiralpak IC (21×250 mm, 5 micron), pure methanol with CO2 70 mL/min)

Sources & evidence

ORD record
ord-d1892d5e625e47448f77dd81cc36b0bd
Source dataset
uspto-grants-2010_11
Patent number
US07842685B2

Reaction notes

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