Dimethylformamide → HCID 57418440, compound

HRID 1868138Notes

Reaction equation

HRID 1868138 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:13][CH2:12][N:11]([S:14]([C:17]3[S:21][C:20]([C:22](O)=[O:23])=[CH:19][CH:18]=3)(=[O:16])=[O:15])[C@H:10]([CH3:25])[CH2:9]2)=[C:4]([C:26]([F:29])([F:28])[F:27])[CH:3]=1.C(Cl)(C(Cl)=O)=O.[CH3:36][N:37](C=O)[CH3:38]>C(Cl)Cl>[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:13][CH2:12][N:11]([S:14]([C:17]3[S:21][C:20]([C:22]([N:37]([CH3:38])[CH3:36])=[O:23])=[CH:19][CH:18]=3)(=[O:15])=[O:16])[C@H:10]([CH3:25])[CH2:9]2)=[C:4]([C:26]([F:29])([F:28])[F:27])[CH:3]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 57418436HCID 57418436, compound

Product 1

HCID 57418440HCID 57418440, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 5-({(2R)-4-[4-fluoro-2-(trifluoromethyl)phenyl]-2-methylpiperazin-1-yl}sulfonyl)thiophene-2-carboxylic acid (260 mg, 0.575 mmol) in DCM (5 mL) was added (COCl)2 (150.5 μL, 1.726 mmol) and DMF (1 small drop). The resultant mixture was stirred for 3 h. The solvent was evaporated and the crude residue was redissolved in dioxane (5 mL). To this was added 2N NH3 in EtOH (2 mL). The reaction mixture was stirred for 6 h then concentrated. The crude product was purified on SiO2 column eluted with hexanes/EtOAc to give the titled compound (less polar fraction, a side product) as a light yellow solid (48 mg, 17%). HRMS: calcd for C19H21F4N3O3S2+H+, 480.10332. found (ESI-FTMS, [M+H]1+), 480.1042.

Workup

  1. customThe solvent was evaporated
  2. dissolutionthe crude residue was redissolved in dioxane (5 mL)
  3. additionTo this was added 2N NH3 in EtOH (2 mL)
  4. concentrationthen concentrated
  5. customThe crude product was purified on SiO2 column
  6. washeluted with hexanes/EtOAc

Sources & evidence

ORD record
ord-8ee9cbb5f4274e1eb881e6c168145e39
Source dataset
uspto-grants-2009_12
Patent number
US07632838B2

Reaction notes

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