Dimethyl Sulfoxide → n-(4-(2-Formyl-6-(4-(trifluoromethyl)phenyl)pyrimidin-4-yloxy)benzo[d]thiazol-2-yl)acetamide

HRID 2056705Notes

Reaction equation

HRID 2056705 reaction equation
[OH:1][CH2:2][C:3]1[N:8]=[C:7]([O:9][C:10]2[C:15]3[N:16]=[C:17]([NH:19][C:20](=[O:22])[CH3:21])[S:18][C:14]=3[CH:13]=[CH:12][CH:11]=2)[CH:6]=[C:5]([C:23]2[CH:28]=[CH:27][C:26]([C:29]([F:32])([F:31])[F:30])=[CH:25][CH:24]=2)[N:4]=1.C(Cl)(=O)C(Cl)=O.CS(C)=O.C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH:2]([C:3]1[N:8]=[C:7]([O:9][C:10]2[C:15]3[N:16]=[C:17]([NH:19][C:20](=[O:22])[CH3:21])[S:18][C:14]=3[CH:13]=[CH:12][CH:11]=2)[CH:6]=[C:5]([C:23]2[CH:28]=[CH:27][C:26]([C:29]([F:31])([F:32])[F:30])=[CH:25][CH:24]=2)[N:4]=1)=[O:1]

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 6422Trifluoroacetic acidHCID 65578Oxalyl chlorideHCID 11518253N-(4-(2-(Hydroxymethyl)-6-(4-(trifluoromethyl)phenyl)pyrimidin-4-yloxy)-benzo[d]thiazol-2-yl)acetamide

Product 1

HCID 58612017n-(4-(2-Formyl-6-(4-(trifluoromethyl)phenyl)pyrimidin-4-yloxy)benzo[d]thiazol-2-yl)acetamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
-78 °C

Procedure

To a solution of N-(4-(2-(hydroxymethyl)-6-(4-(trifluoromethyl)phenyl)-pyrimidin-4-yloxy)benzo[d]thiazol-2-yl)acetamide (80 mg, 0.174 mmol, Example 98) in DCM (2 mL) was added oxalyl chloride (0.35 mL, 2M solution in DCM, 0.7 mmol, Aldrich). The mixture was cooled to −78° C., and a solution of DMSO (0.1 mL, 1.4 mmol) in DCM (0.5 mL) was added dropwise with stirring. The reaction mixture was stirred at −78° C. for 2 h, TFA (141 mg, 1.4 mmol) was added dropwise, and the mixture was allowed to reach room temperature. The reaction mixture was partitioned between water (10 mL) and DCM (10 mL). The organic phase was separated, washed with sat. aqueous solution of sodium bicarbonate, dried over Na2SO4 and filtered. The filtrate was evaporated under reduced pressure to give the crude title compound, which was used in the next step without additional purification. MS (ESI, pos. ion) m/z: 459 (M+1).

Workup

  1. stirringThe reaction mixture was stirred at −78° C. for 2 h
  2. customto reach room temperature
  3. customThe reaction mixture was partitioned between water (10 mL) and DCM (10 mL)
  4. customThe organic phase was separated
  5. washwashed with sat. aqueous solution of sodium bicarbonate
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. customThe filtrate was evaporated under reduced pressure

Sources & evidence

ORD record
ord-cfbb761ed4144400900b8efb941b2b5d
Source dataset
uspto-grants-2008_02
Patent number
US07335672B2

Reaction notes

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