Dimethyl Sulfoxide → HCID 178516777, compound

HRID 1819431Notes

Reaction equation

HRID 1819431 reaction equation
CS(C)=O.C(Cl)(=O)C(Cl)=O.[N+:11]([C:14]1[C:15]([NH:33][CH2:34][C@H:35]2[CH2:40][CH2:39][C@H:38]([N:41]3[CH2:44][CH:43]([OH:45])[CH2:42]3)[CH2:37][CH2:36]2)=[N:16][C:17]([NH:20][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=2[O:28][C:29]([F:32])([F:31])[F:30])=[N:18][CH:19]=1)([O-:13])=[O:12].CCN(CC)CC.[O-]S([O-])(=O)=O.[Na+].[Na+]>C(Cl)Cl>[N+:11]([C:14]1[C:15]([NH:33][CH2:34][C@H:35]2[CH2:36][CH2:37][C@H:38]([N:41]3[CH2:42][C:43](=[O:45])[CH2:44]3)[CH2:39][CH2:40]2)=[N:16][C:17]([NH:20][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=2[O:28][C:29]([F:31])([F:32])[F:30])=[N:18][CH:19]=1)([O-:13])=[O:12]

Participants

7

Reactant 5

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 24436Sodium SulfateHCID 65578Oxalyl chlorideHCID 178526822HCID 178526822, compound

Product 1

HCID 178516777HCID 178516777, compoundYield 74.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

DMSO (170 μL, 2.4 mmol) was added dropwise to a solution of oxalyl chloride (105 μL, 1.2 mmol) in dry CH2Cl2 (10 mL) cooled in a dry ice/acetone bath. The reaction mixture was stirred with cooling for 30 min. A solution of 1-(trans-4-{[(5-nitro-2-{[2-(trifluoromethoxy)benzyl]amino}pyrimidin-4-yl)amino]methyl}cyclohexyl)azetidin-3-ol (200 mg, 0.4 mmol) in dry CH2Cl2 was added dropwise and the reaction was allowed to stir for 2 h. Et3N (501 μL, 3.6 mmol) was then added and the reaction mixture was stirred for 16 h and allowed to slowly warm to room temperature. The mixture was diluted with CH2Cl2 and poured into saturated aqueous Na2SO4. The aqueous phase was separated and extracted with CH2Cl2 (×2). The combined organic phase was dried over Na2SO4, decanted and concentrated. The crude product was purified by flash chromatography on a 120 g SiO2 column, eluting with 90:9:1 CH2Cl2:MeOH:NH4OH as an eluent to afford 147 mg (74%) of the title compound, m/z 495.6 [M+1]+.

Workup

  1. temperaturecooled in a dry ice/acetone bath
  2. temperaturewith cooling for 30 min
  3. stirringto stir for 2 h
  4. stirringthe reaction mixture was stirred for 16 h
  5. customThe aqueous phase was separated
  6. extractionextracted with CH2Cl2 (×2)
  7. dry with materialThe combined organic phase was dried over Na2SO4
  8. customdecanted
  9. concentrationconcentrated
  10. customThe crude product was purified by flash chromatography on a 120 g SiO2 column
  11. washeluting with 90:9:1 CH2Cl2

Sources & evidence

ORD record
ord-7d4b6d15c0194a89a5c6e59dfbd2337a
Source dataset
uspto-grants-2009_10
Patent number
US07601714B2

Reaction notes

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