(Diethylamino)sulfur trifluoride → HCID 86621267, compound

HRID 1717590Notes

Reaction equation

HRID 1717590 reaction equation
[F:1][C:2]1[C:3]([NH:27][C:28]2[CH:33]=[CH:32][C:31]([I:34])=[CH:30][C:29]=2[F:35])=[C:4]([C:9]([N:11]2[CH2:14][C:13]([CH2:16][N:17]([CH2:25][CH3:26])[C:18](=[O:24])[O:19][C:20]([CH3:23])([CH3:22])[CH3:21])(O)[CH2:12]2)=[O:10])[CH:5]=[CH:6][C:7]=1[F:8].CCN(S(F)(F)[F:42])CC>C(Cl)(Cl)Cl>[F:1][C:2]1[C:3]([NH:27][C:28]2[CH:33]=[CH:32][C:31]([I:34])=[CH:30][C:29]=2[F:35])=[C:4]([C:9]([N:11]2[CH2:12][C:13]([CH2:16][N:17]([CH2:25][CH3:26])[C:18](=[O:24])[O:19][C:20]([CH3:23])([CH3:21])[CH3:22])([F:42])[CH2:14]2)=[O:10])[CH:5]=[CH:6][C:7]=1[F:8]

Participants

4

Reactant 2

HCID 123472(Diethylamino)sulfur trifluorideHCID 69113810HCID 69113810, compound

Product 1

HCID 86621267HCID 86621267, compoundYield 71.1%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To 1,1-dimethylethyl [{1-({3,4-difluoro-2-[(2-fluoro-4-iodophenyl)amino]phenyl}carbonyl)-3-hydroxyazetidin-3-yl]methyl}ethylcarbamate (27 mg, 0.044 mmol), prepared using procedures similar to those in Example 3 and followed by Boc-protection, in chloroform (2.5 mL) added DAST (11.8 μL, 0.089 mmol) and stirred for 3.5 hr at room temperature. Quenched with water (15 mL), partitioned phases and extracted aqueous phase with chloroform (2×15 mL). The combined chloroform extracts were dried over sodium sulfate, filtered and the filtrate concentrated in vacuo. The residue was purified on a silica gel column to afford 1,1-dimethylethyl [{1-({3,4-difluoro-2-[(2-fluoro-4-iodophenyl)amino]phenyl}carbonyl)-3-fluoroazetidin-3-yl]methyl}ethylcarbamate (19.0 mg, 70%).

Workup

  1. customQuenched with water (15 mL)
  2. custompartitioned phases
  3. extractionextracted aqueous phase with chloroform (2×15 mL)
  4. dry with materialThe combined chloroform extracts were dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationthe filtrate concentrated in vacuo
  7. customThe residue was purified on a silica gel column

Sources & evidence

ORD record
ord-9ec6a120067043e1a59cdd1bdb8763a0
Source dataset
uspto-grants-2010_09
Patent number
US07803839B2

Reaction notes

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