Hydrochloric Acid → HCID 16074842, compound

HRID 1015662Notes

Reaction equation

HRID 1015662 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([N:14]([C:25]2[CH:29]=[C:28]([C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)[S:27][C:26]=2[C:36]([OH:38])=[O:37])[C:15](=[O:24])[C:16]2[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][C:17]=2[Cl:23])[CH2:10][CH2:9]1)=O)(C)(C)C.Cl>O1CCOCC1>[Cl:23][C:17]1[CH:18]=[C:19]([Cl:22])[CH:20]=[CH:21][C:16]=1[C:15]([N:14]([CH:11]1[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]1)[C:25]1[CH:29]=[C:28]([C:30]2[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=2)[S:27][C:26]=1[C:36]([OH:38])=[O:37])=[O:24]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 16074838HCID 16074838, compound

Product 1

HCID 16074842HCID 16074842, compoundYield 107.2%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A solution of 4-[(2-Carboxy-5-phenyl-thiophen-3-yl)-(2,4-dichloro-benzoyl)-amino]-piperidine-1-carboxylic acid tert-butyl ester (240 mg, 0.42 mmol) in dioxane (4 ml) at 21° C. under nitrogen was treated with anhydrous 4M HCl (3 ml, 12.6 mmol, 30 eq). After 4 h the reaction was stripped off solvent and the residue triturated with ether to give 3-[(2,4-Dichloro-benzoyl)-piperidin-4-yl-amino]-5-phenyl-thiophene-2-carboxylic acid as a pale yellow powder (214 mg, 100%) 1H NMR (Acetone, 400 MHz) 7.76-7.73 (m, 2H), 7.64 (s, 1H), 7.45-7.38 (m, 3H), 7.30 (bs, 1H), 7.28-7.24 (m, 1H), 4.93-4.84 (m, 1H), 3.56-3.49 (m, 2H), 3.25-3.14 (m, 2H), 3.05-2.55 (bs, 1H), 2.50-2.37 (m, 2H), 2.13-1.83 (m, 1H).

Workup

  1. customsolvent and the residue triturated with ether

Sources & evidence

ORD record
ord-ef999aa4d9e44ddfa7bd45133d6645eb
Source dataset
uspto-grants-2011_07
Patent number
US07985769B2

Reaction notes

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