HCID 178522184, compound → 4-(4-{4-[(2-Phenyl-5-trifluoromethyl-oxazole-4-carbonyl)-amino]-phenyl}-[1,4]diazepane-1-carbonyl)-cyclohexanecarboxylic acid

HRID 1509875Notes

Reaction equation

HRID 1509875 reaction equation
C([O:8][C:9]([C@H:11]1[CH2:16][CH2:15][C@@H:14]([C:17]([N:19]2[CH2:25][CH2:24][CH2:23][N:22]([C:26]3[CH:31]=[CH:30][C:29]([NH:32][C:33]([C:35]4[N:36]=[C:37]([C:44]5[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=5)[O:38][C:39]=4[C:40]([F:43])([F:42])[F:41])=[O:34])=[CH:28][CH:27]=3)[CH2:21][CH2:20]2)=[O:18])[CH2:13][CH2:12]1)=[O:10])C1C=CC=CC=1>CO.[Pd]>[C:44]1([C:37]2[O:38][C:39]([C:40]([F:41])([F:42])[F:43])=[C:35]([C:33]([NH:32][C:29]3[CH:30]=[CH:31][C:26]([N:22]4[CH2:23][CH2:24][CH2:25][N:19]([C:17]([CH:14]5[CH2:13][CH2:12][CH:11]([C:9]([OH:10])=[O:8])[CH2:16][CH2:15]5)=[O:18])[CH2:20][CH2:21]4)=[CH:27][CH:28]=3)=[O:34])[N:36]=2)[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=1

Participants

4

Reactant 1

HCID 178522184HCID 178522184, compound

Product 1

HCID 446288514-(4-{4-[(2-Phenyl-5-trifluoromethyl-oxazole-4-carbonyl)-amino]-phenyl}-[1,4]diazepane-1-carbonyl)-cyclohexanecarboxylic acidYield 40%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Cis-4-(4-{4-[(2-Phenyl-5-trifluoromethyl-oxazole-4-carbonyl)-amino]-phenyl}-[1,4]diazepane-1-carbonyl)-cyclohexanecarboxylic acid benzyl ester (90 mg) was diluted in 30 mL of methanol and 100 mg of Pd/C (10%) was added. The mixture was placed on a Parr shaker for hydrogenation at 50 psi for 3 hr. The mixture was filtered and the solvent was removed to afford the product 4-(4-{4-[(2-phenyl-5-trifluoromethyl-oxazole-4-carbonyl)-amino]-phenyl}-[1,4]diazepane-1-carbonyl)-cyclohexanecarboxylic acid (30 mg, 40% yield) as a white solid. LCMS for C30H31F3N4O5 calcd. (m/e) 584, observed 585 (M+H).

Workup

  1. filtrationThe mixture was filtered
  2. customthe solvent was removed

Sources & evidence

ORD record
ord-7b5a1ef3b64a47558dd2b0e8db297056
Source dataset
uspto-grants-2012_07
Patent number
US08211884B2

Reaction notes

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