HCID 16074975, compound → HCID 16074983, compound

HRID 1015644Notes

Reaction equation

HRID 1015644 reaction equation
C(OC([N:11]1[CH2:16][CH2:15][CH:14]([CH2:17][N:18]([C:29]2[CH:33]=[C:32]([C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=3)[S:31][C:30]=2[C:40]([OH:42])=[O:41])[C:19](=[O:28])[C:20]2[CH:25]=[CH:24][C:23]([Cl:26])=[CH:22][C:21]=2[Cl:27])[CH2:13][CH2:12]1)=O)C1C=CC=CC=1>CO.[Pd]>[Cl:27][C:21]1[CH:22]=[C:23]([Cl:26])[CH:24]=[CH:25][C:20]=1[C:19]([N:18]([CH2:17][CH:14]1[CH2:13][CH2:12][NH:11][CH2:16][CH2:15]1)[C:29]1[CH:33]=[C:32]([C:34]2[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=2)[S:31][C:30]=1[C:40]([OH:42])=[O:41])=[O:28]

Participants

4

Reactant 1

HCID 16074975HCID 16074975, compound

Product 1

HCID 16074983HCID 16074983, compoundYield 18%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

4-{[(2-Carboxy-5-phenyl-thiophen-3-yl)-(2,4-dichloro-benzoyl)-amino]-methyl}-piperidine-1-carboxylic acid benzyl ester (124 mg, 0.2 mmol) was dissolved in MeOH (2 mL) and treated with 10% Pd/C (200 mg) under H2 balloon. The reaction was stirred at room temperature for 18 h and the mixture was filtered on celite. The solution was evaporated to a residue that was purified by reverse-phase HPLC to provide 3-[(2,4-Dichloro-benzoyl)-piperidin-4-ylmethyl-amino]-5-phenyl-thiophene-2-carboxylic acid (17.3 mg, 18% yield). 1H NMR (CD3OD, 300 MHz): 7.55 (d, 1 H), 7.50 (m, 2 H), 7.27-7.39 (m, 4 H), 7.25 (s, 1 H), 7.18 (dd, 1 H), 4.12 (m, 1 H), 3.75 (m, 1 H), 3.43 (m, 2H), 2.96 (q, 2 H), 2.65 (d, 2 H), 2.05 (m, 1 H), 1.62 (m, 2 H).

Workup

  1. filtrationthe mixture was filtered on celite
  2. customThe solution was evaporated to a residue that
  3. customwas purified by reverse-phase HPLC

Sources & evidence

ORD record
ord-97932f1fe7f1461b8c37a7fe731495c4
Source dataset
uspto-grants-2011_07
Patent number
US07985769B2

Reaction notes

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