HCID 131732272, compound → HCID 131732273, compound

HRID 2272309Notes

Reaction equation

HRID 2272309 reaction equation
C([O:8][C:9]1[CH:14]=[CH:13][C:12]([N:15]([C:20]2[C:39]([CH:40]3[CH2:42][CH2:41]3)=[CH:38][C:23]3[C:24]([C:34]([NH:36][CH3:37])=[O:35])=[C:25]([C:27]4[CH:32]=[CH:31][C:30]([Cl:33])=[CH:29][CH:28]=4)[O:26][C:22]=3[CH:21]=2)[S:16]([CH3:19])(=[O:18])=[O:17])=[CH:11][C:10]=1[F:43])C1C=CC=CC=1>C(OCC)(=O)C.C(O)C.[Pd]>[Cl:33][C:30]1[CH:31]=[CH:32][C:27]([C:25]2[O:26][C:22]3[CH:21]=[C:20]([N:15]([C:12]4[CH:13]=[CH:14][C:9]([OH:8])=[C:10]([F:43])[CH:11]=4)[S:16]([CH3:19])(=[O:18])=[O:17])[C:39]([CH:40]4[CH2:41][CH2:42]4)=[CH:38][C:23]=3[C:24]=2[C:34]([NH:36][CH3:37])=[O:35])=[CH:28][CH:29]=1

Participants

5

Reactant 1

HCID 131732272HCID 131732272, compound

Product 1

HCID 131732273HCID 131732273, compound

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

6-(N-(4-(benzyloxy)-3-fluorophenyl)methylsulfonamido)-2-(4-chlorophenyl)-5-cyclopropyl-N-methylbenzofuran-3-carboxamide (350 mg, 0.565 mmol) was dissolved in ethyl acetate (8.0 mL) and ethanol (8.0 mL). 10% of Pd/C (30.1 mg, 0.283 mmol) was added followed by the addition of H2 (1 atmosphere, balloon). The mixture was stirred for 2 h at RT and filtrated through Celite. The filtrate was concentrated to dryness and rinsed twice with hexane to give the desired product as a white solid which was used without further purification. LCMS (m/z, ES+)=529 (M+H+).

Workup

  1. additionfollowed by the addition of H2 (1 atmosphere, balloon)
  2. filtrationfiltrated through Celite
  3. concentrationThe filtrate was concentrated to dryness
  4. washrinsed twice with hexane

Sources & evidence

ORD record
ord-39c788d6690346e39b385015575057b7
Source dataset
uspto-grants-2015_09
Patent number
US09119868B2

Reaction notes

Loading…