Triethylamine → HCID 18473245, compound

HRID 2227389Notes

Reaction equation

HRID 2227389 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([C:9]([NH:20][S:21]([C:23]([CH3:26])([CH3:25])[CH3:24])=[O:22])([C:14]2[N:18]([CH3:19])[CH:17]=[N:16][CH:15]=2)[CH2:10][CH2:11][CH2:12][OH:13])=[CH:5][C:4]=1[F:27])#[N:2].CCN(CC)CC>CS(C)=O.C(Cl)Cl>[C:1]([C:3]1[CH:8]=[CH:7][C:6]([C:9]([NH:20][S:21]([C:23]([CH3:25])([CH3:24])[CH3:26])=[O:22])([C:14]2[N:18]([CH3:19])[CH:17]=[N:16][CH:15]=2)[CH2:10][CH2:11][CH:12]=[O:13])=[CH:5][C:4]=1[F:27])#[N:2]

Participants

5

Reactant 2

HCID 8471TriethylamineHCID 18473232HCID 18473232, compound

Product 1

HCID 18473245HCID 18473245, compound

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 6344DichloromethaneSolvent

Procedure

Sulfur trioxide pyridine complex (0.775 g, 4.866 mmol) in DMSO (5 mL) was added to a solution of (N-[1-(4-cyano-3-fluorophenyl)-4-hydroxy-1-(1-methyl-1H-imidazol-5-yl)butyl]-2-methylpropane-2-sulfinamide (0.382 g, 0.973 mmol) and Et3N (1.36 mL, 0.985 mmol) in CH2Cl2 (15 mL) at 0° C. in an ice-H2O bath, then left to come to room temperature overnight. The reaction mixture was partitioned between CH2Cl2 and aqueous saturated NaHCO3 solution, the aqueous layer washed with CH2Cl2 (3×), the organic layers combined and dried (MgSO4), filtered and concentrated to give the crude product. Purification on an ISCO Combiflash eluting with 2-6% MeOH/CH2Cl2 gave the title compound. MS(M+1) 391.

Workup

  1. waitleft
  2. customThe reaction mixture was partitioned between CH2Cl2 and aqueous saturated NaHCO3 solution
  3. washthe aqueous layer washed with CH2Cl2 (3×)
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto give the crude product
  8. customPurification on an ISCO Combiflash
  9. washeluting with 2-6% MeOH/CH2Cl2

Sources & evidence

ORD record
ord-37972e5b578f47d38fda6da84241cc07
Source dataset
uspto-grants-2002_07
Patent number
US06413964B1

Reaction notes

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