Hexane → HCID 25167324, compound

HRID 1177850Notes

Reaction equation

HRID 1177850 reaction equation
C([O:8][C:9]1[CH:45]=[CH:44][C:12]([O:13][C:14]2[CH:43]=[CH:42][C:17]([C:18]([NH:20][CH2:21][C:22](=[O:41])[N:23]3[CH2:28][CH2:27][N:26]([C:29](=[O:40])[C:30]4[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=4[C:36]([F:39])([F:38])[F:37])[CH2:25][CH2:24]3)=[O:19])=[CH:16][CH:15]=2)=[CH:11][CH:10]=1)C1C=CC=CC=1.CCCCCC>[Pd].CO>[OH:8][C:9]1[CH:45]=[CH:44][C:12]([O:13][C:14]2[CH:15]=[CH:16][C:17]([C:18]([NH:20][CH2:21][C:22](=[O:41])[N:23]3[CH2:24][CH2:25][N:26]([C:29](=[O:40])[C:30]4[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=4[C:36]([F:39])([F:38])[F:37])[CH2:27][CH2:28]3)=[O:19])=[CH:42][CH:43]=2)=[CH:11][CH:10]=1

Participants

5

Reactant 2

HCID 8058HexaneHCID 57855674HCID 57855674, compound

Product 1

HCID 25167324HCID 25167324, compoundYield 48.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Pd/C (20 mg in 3 drops of water) was added to 4-(4-benzyloxy-phenoxy)-N-{2-oxo-2-[4-(2-trifluoromethyl-benzoyl)-piperazin-1-yl]-ethyl}-benzamide (80 mg, 0.13 mmol) in MeOH (10 mL). The resulting reaction mixture was stirred at room temperature under an atmosphere of hydrogen for 3 hours. The reaction mixture was then filtered through a bed of celite. The methanol was removed to afford 80 mg of crude product. Purification by column chromatography (using silica gel of mesh size of 60-120 and 80/20 EtOAc:Hexane as the eluent) afforded 33 mg (48% yield) of 4-(4-hydroxy-phenoxy)-N-{2-oxo-2-[4-(2-trifluoromethyl-benzoyl)-piperazin-1-yl]-ethyl}-benzamide LC-MS purity: 93%. 1H NMR (DMSO-D6): δ 9.4 (s, 1H), 8.5 (t, 1H), 7.9-7.5 (m, 6H), 6.8-7 (m, 5H), 4.2 (d, 2H), 3.5 (m, 6H), 3.1 (m, 2H).

Workup

  1. customThe resulting reaction mixture
  2. filtrationThe reaction mixture was then filtered through a bed of celite
  3. customThe methanol was removed
  4. customto afford 80 mg of crude product
  5. customPurification by column chromatography (

Sources & evidence

ORD record
ord-ddeb793f075e49d2833eeea870debed2
Source dataset
uspto-grants-2010_11
Patent number
US07842696B2

Reaction notes

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