Dimethyl Sulfoxide → HCID 58902313, compound

HRID 1640191Notes

Reaction equation

HRID 1640191 reaction equation
C(Cl)(=O)C(Cl)=O.CS(C)=O.[OH:11][CH2:12][C:13]1[CH:18]=[C:17]([O:19][C:20]2[CH:29]=[C:28]3[C:23]([CH2:24][CH2:25][CH:26]([C:30]([NH:32][C:33]4[CH:34]=[C:35]([CH:45]=[C:46]([C:48]([F:51])([F:50])[F:49])[CH:47]=4)[CH2:36][NH:37][C:38](=[O:44])[O:39][C:40]([CH3:43])([CH3:42])[CH3:41])=[O:31])[CH2:27]3)=[CH:22][CH:21]=2)[CH:16]=[CH:15][N:14]=1.O>C(Cl)Cl>[CH:12]([C:13]1[CH:18]=[C:17]([O:19][C:20]2[CH:29]=[C:28]3[C:23]([CH2:24][CH2:25][CH:26]([C:30]([NH:32][C:33]4[CH:34]=[C:35]([CH:45]=[C:46]([C:48]([F:51])([F:49])[F:50])[CH:47]=4)[CH2:36][NH:37][C:38](=[O:44])[O:39][C:40]([CH3:43])([CH3:42])[CH3:41])=[O:31])[CH2:27]3)=[CH:22][CH:21]=2)[CH:16]=[CH:15][N:14]=1)=[O:11]

Participants

6

Reactant 4

HCID 679Dimethyl Sulfoxide2×HCID 962WaterHCID 65578Oxalyl chloride2×HCID 58902218HCID 58902218, compound

Product 1

HCID 58902313HCID 58902313, compoundYield 98.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent5×

Conditions

Temperature
-78 °C

Procedure

To a solution of oxalyl chloride (0.086 mL, 1.02 mmol) in DCM (4 mL) at −78° C., was added a solution of DMSO (0.109 mL, 1.53 mmol) in DCM (1 mL) dropwise. The reaction mixture was allowed to stir at −78° C. for 30 min, and then a solution of tert-butyl [3-{[(7-{[2-(hydroxymethyl)pyridin-4-yl]oxy}-1,2,3,4-tetrahydronaphthalen-2-yl)carbonyl]amino}-5-(trifluoromethyl)benzyl]carbamate (292 mg, 0.51 mmol) in DCM (1 mL) was added dropwise. After 45 min. the reaction was incomplete. In a separate flask, oxalyl chloride (0.086 mL, 1.02 mmol) and DCM (4 mL) were cooled to −78° C., and a solution of DMSO (0.109 mL, 1.53 mmol) in DCM (1.00 mL) was added dropwise. The solution was stirred at −78° C. for 15 min, and then transferred via cannula to the reaction mixture and allowed to stir for 1 h. TEA (0.712 mL, 5.11 mmol) was added and the mixture was allowed to warm to rt. Water was added and the layers were separated. The organic solution was washed with brine, dried over Na2SO4, filtered and concentrated to give tert-butyl [3-[({7-[(2-formylpyridin-4-yl)oxy]-1,2,3,4-tetrahydronaphthalen-2-yl}carbonyl)amino]-5-(trifluoromethyl)benzyl]carbamate (285 mg, 97.9%). LCMS: (FA) ES+ 570.4.

Workup

  1. waitAfter 45 min. the reaction was incomplete
  2. stirringThe solution was stirred at −78° C. for 15 min
  3. stirringto stir for 1 h
  4. temperatureto warm to rt
  5. customthe layers were separated
  6. washThe organic solution was washed with brine
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-6b1fa55e05834e9f95dbce45c7684e26
Source dataset
uspto-grants-2012_02
Patent number
US08110687B2

Reaction notes

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