Reaction #619173

ord-9c3fc7b8404b4913994c2f23dfc02c57

Reaction equation

Nc1ncc(C=O)s1
5-formyl-2-aminothiazole
CC1CCC(NC2CCN(C(=O)OC(C)(C)C)CC2)CC1
4-(4-methyl-cyclohexylamino)-piperidine-1-carboxylic acid tert-butyl ester
O=C(n1ccnc1)n1ccnc1
CDI
→
CC1CCC(N(C(=O)Nc2ncc(C=O)s2)C2CCN(C(=O)OC(C)(C)C)CC2)CC1
desired product
CC1CCC(N(C(=O)Nc2ncc(C=O)s2)C2CCN(C(=O)OC(C)(C)C)CC2)CC1
4-[3-(5-Formyl-thiazol-2-yl)-1-(4-methyl-cyclohexyl)-ureido]-piperidine-1-carboxylic acid tert-butyl ester

Reactants

Nc1ncc(C=O)s1
5-formyl-2-aminothiazole
CC1CCC(NC2CCN(C(=O)OC(C)(C)C)CC2)CC1
4-(4-methyl-cyclohexylamino)-piperidine-1-carboxylic acid tert-butyl ester
O=C(n1ccnc1)n1ccnc1
CDI

Reagents

CN(C)c1ccncc1
DMAP

Solvents

C1CCOC1
THF

Conditions

Temperature
65°CELSIUS
Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    OtherPrepared in a manner similar to general procedure (C)

Procedure

Prepared in a manner similar to general procedure (C) using 5-formyl-2-aminothiazole (1.88 g, 14.6 mmol), 4-(4-methyl-cyclohexylamino)-piperidine-1-carboxylic acid tert-butyl ester (4.32 mg, 14.6 mmol), catalytic DMAP, CDI (2.60 g, 1.1 mmol) and THF with heating to 65° C. afforded 1.77 g (27%) of the desired product after purification.

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: USRE045183E1uspto-grants-2014_10