Thionyl Chloride → HCID 51352133, compound

HRID 1512694Notes

Reaction equation

HRID 1512694 reaction equation
[F:1][C:2]([F:36])([CH2:28][CH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)[CH2:3][C:4]1[C:5]([CH3:27])=[N:6][O:7][C:8]=1[C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:20]=[CH:19][C:18]([C:21]3([C:24](O)=[O:25])[CH2:23][CH2:22]3)=[CH:17][CH:16]=2)=[CH:11][CH:10]=1.S(Cl)(Cl)=O.[CH3:41][S:42]([NH2:45])(=[O:44])=[O:43].[H-].[Na+]>C(Cl)Cl.C1COCC1.CCOC(C)=O>[F:1][C:2]([F:36])([CH2:28][CH2:29][C:30]1[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=1)[CH2:3][C:4]1[C:5]([CH3:27])=[N:6][O:7][C:8]=1[C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:20]=[CH:19][C:18]([C:21]3([C:24]([NH:45][S:42]([CH3:41])(=[O:44])=[O:43])=[O:25])[CH2:23][CH2:22]3)=[CH:17][CH:16]=2)=[CH:11][CH:10]=1

Participants

8

Reactant 4

HCID 24386Thionyl ChlorideHCID 24758Sodium hydride2×HCID 72879MethanesulfonamideHCID 51352481HCID 51352481, compound

Product 1

HCID 51352133HCID 51352133, compound

Reagents, catalysts & solvents 3

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

1-{4′-[4-(2,2-Difluoro-4-phenyl-butyl)-3-methyl-isoxazol-5-yl]-biphenyl-4-yl}-cyclopropanecarboxylic acid (0.225 g, 0.441 mmol) was dissolved in CH2Cl2 (2.3 mL) and thionyl chloride (0.07 mL, 0.971 mmol) was added. After 30 minutes the reaction was concentrated. Separately, methanesulfonamide (0.124 g, 1.30 mmol) was dissolved in THF (2 mL) and sodium hydride (60% in mineral oil, 0.044 g, 1.103 mmol) was added. The acid chloride from the first reaction was dissolved in THF and carefully added to the second mixture. The reaction was monitored by analytical LCMS and excess sodium hydride was added until the reaction went to completion. Standard aqueous workup and silica gel chromatography (0-100% EtOAc in hexanes) afforded the title compound.

Workup

  1. concentrationAfter 30 minutes the reaction was concentrated
  2. additioncarefully added to the second mixture
  3. additionwas added until the reaction

Sources & evidence

ORD record
ord-411410fc2c0b4c03a600c57ed0d62fc8
Source dataset
uspto-grants-2012_07
Patent number
US08217066B2

Reaction notes

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