Acetic Acid → 4-[2-(3,3-Dicyclohexyl-ureido)-4-methyl-thiazole-5-sulfonylamino]-piperidine-1-carboxylic acid ethyl ester

HRID 531940Notes

Reaction equation

HRID 531940 reaction equation
[NH2:1][CH:2]1[CH2:7][CH2:6][N:5]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH2:4][CH2:3]1.[CH:13]1([NH:19][CH:20]2[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]2)[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1.[C:26]([NH:29][C:30]1[S:31][C:32]([S:35](Cl)(=[O:37])=[O:36])=[CH:33][N:34]=1)(=[O:28])C.Br.[C:40](O)(=O)C>>[CH2:11]([O:10][C:8]([N:5]1[CH2:4][CH2:3][CH:2]([NH:1][S:35]([C:32]2[S:31][C:30]([NH:29][C:26]([N:19]([CH:13]3[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18]3)[CH:20]3[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25]3)=[O:28])=[N:34][C:33]=2[CH3:40])(=[O:37])=[O:36])[CH2:7][CH2:6]1)=[O:9])[CH3:12].[NH:5]1[CH2:4][CH2:3][CH:2]([NH:1][S:35]([C:32]2[S:31][C:30]([NH:29][C:26]([N:19]([CH:13]3[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18]3)[CH:20]3[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25]3)=[O:28])=[N:34][C:33]=2[CH3:40])(=[O:37])=[O:36])[CH2:7][CH2:6]1

Participants

7

Reactant 5

HCID 176Acetic AcidHCID 260Hydrogen BromideHCID 7582DicyclohexylamineHCID 100867Ethyl 4-amino-1-piperidinecarboxylateHCID 3502612-Acetamido-1,3-thiazole-5-sulfonyl chloride

Product 2

HCID 578836294-[2-(3,3-Dicyclohexyl-ureido)-4-methyl-thiazole-5-sulfonylamino]-piperidine-1-carboxylic acid ethyl esterHCID 578838592-(3,3-Dicyclohexylureido)-4-methylthiazole-5-sulfonic acid piperidin-4-ylamide

Procedure

4-[2-(3,3-Dicyclohexyl-ureido)-4-methyl-thiazole-5-sulfonylamino]-piperidine-1-carboxylic acid ethyl ester was prepared as described in Example 173 using ethyl 4-amino-1-piperidine carboxylate, dicyclohexylamine and 2-acetylamino-thiazole-5-sulfonyl chloride. Reaction with 33% HBr in acetic acid followed by chromatography afforded the title compound.

Sources & evidence

ORD record
ord-5575f1b89a064cef8392e9264748b161
Source dataset
uspto-grants-2014_10
Patent number
USRE045183E1

Reaction notes

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