Dimethylcarbamoyl Chloride → HCID 57688329, compound

HRID 731416Notes

Reaction equation

HRID 731416 reaction equation
C([O:3][C:4](=[O:28])[CH2:5][S:6][C:7]1[S:11][C:10]([NH:12][C:13]([N:15]([CH:22]2[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]2)[CH:16]2[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]2)=[O:14])=[N:9][CH:8]=1)C.[C:29]([N:36]1[CH2:41]CCC[C:37]1=O)(OC(C)(C)C)=[O:30].C1(N)CCCCC1.C(OC(=O)CSC1SC(N)=NC=1)C.CN(C)C(Cl)=O>>[CH:22]1([N:15]([CH:16]2[CH2:21][CH2:20][N:19]([C:29](=[O:30])[N:36]([CH3:41])[CH3:37])[CH2:18][CH2:17]2)[C:13](=[O:14])[NH:12][C:10]2[S:11][C:7]([S:6][CH2:5][C:4]([OH:3])=[O:28])=[CH:8][N:9]=2)[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]1

Participants

6

Reactant 5

HCID 6598Dimethylcarbamoyl ChlorideHCID 7965CyclohexylamineHCID 7577838tert-Butyl 2-oxopiperidine-1-carboxylateHCID 21455623Ethyl 2-(2-aminothiazol-5-ylthio)acetateHCID 86630188HCID 86630188, compound

Product 1

HCID 57688329HCID 57688329, compound

Procedure

{2-[3-Cyclohexyl-3-piperidin-4-yl-ureido]-thiazol-5-ylsulfanyl}-acetic acid ethyl ester was pre-pared in a similar manner to the synthesis of example 12 from N-Boc piperidone, cyclohexyl-amine and (2-amino-thiazol-5-ylsulfanyl)-acetic acid ethyl ester, Boc deprotection, reaction with dimethylcarbamoyl chloride and hydrolysis of the ester moiety as described in general procedure (I) gave the title compound.

Sources & evidence

ORD record
ord-627c1e00e73646249f3f2b8700654ef9
Source dataset
uspto-grants-2009_09
Patent number
US07582769B2

Reaction notes

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