HCID 178499315, compound → HCID 178499313, compound

HRID 1808013Notes

Reaction equation

HRID 1808013 reaction equation
C(OC([N:11]1[CH2:16][CH2:15][CH:14]([N:17]([C:27]2[CH:31]=[CH:30][S:29][C:28]=2[C:32]([O:34][CH3:35])=[O:33])[C:18]([C@H:20]2[CH2:25][CH2:24][C@H:23]([CH3:26])[CH2:22][CH2:21]2)=[O:19])[CH2:13][CH2:12]1)=O)C1C=CC=CC=1>CCOC(C)=O.[Pd]>[CH3:35][O:34][C:32]([C:28]1[S:29][CH:30]=[CH:31][C:27]=1[N:17]([C:18]([C@H:20]1[CH2:21][CH2:22][C@H:23]([CH3:26])[CH2:24][CH2:25]1)=[O:19])[CH:14]1[CH2:13][CH2:12][NH:11][CH2:16][CH2:15]1)=[O:33]

Participants

4

Reactant 1

HCID 178499315HCID 178499315, compound

Product 1

HCID 178499313HCID 178499313, compoundYield 45.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

Hydrogenation of 4-[(2-methoxycarbonyl-thiophen-3-yl)-(trans-4-methyl-cyclohexanecarbonyl)-amino]-piperidine-1-carboxylic acid benzyl ester (3.0 g, 6.02 mmol) with Pd/black in EtOAc was carried out for 36 h at 40 psi was carried out as described for example 19, step III gave 3-[(trans-4-methyl-cyclohexanecarbonyl)-piperidin-4-yl-amino]-thiophene-2-carboxylic acid methyl ester (1.0 g, 45.6%). NMR 1H (CDCl3, 400 MHz): 7.525 (d, J=5.3, 1H), 6.84 (d, J=5.3, 1H), 4.674 (tt, 1H), 3.81 (s, 3H), 3.1-2.94 (m, 2H), 2.74-2.6 (m, 2H), 2.26-2.2 (m, 1H), 1.9-1.0 (m, 11H), 0.75 (d, J=6.6, 3H), 0.7-0.5 (m, 2H).

Sources & evidence

ORD record
ord-36c60fafa84f420297e28775158e6f9d
Source dataset
uspto-grants-2013_01
Patent number
US08357718B2

Reaction notes

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