Cyclohexylamine → HCID 57688243, compound

HRID 731414Notes

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(N1CCCCC1=O)(OC(C)(C)C)=O.C1(N)CCCCC1.[CH3:50][N:51]([CH3:56])[S:52](Cl)(=[O:54])=[O:53]>>[CH:22]1([N:15]([CH:16]2[CH2:21][CH2:20][N:19]([S:52](=[O:54])(=[O:53])[N:51]([CH3:56])[CH3:50])[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

Reactant 4

HCID 7965Cyclohexylamine

HCID 83372Dimethylsulphamoyl chloride

HCID 7577838tert-Butyl 2-oxopiperidine-1-carboxylate

HCID 86630188HCID 86630188, compound

Product 1

HCID 57688243HCID 57688243, 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, cyclo-hexylamine and (2-amino-thiazol-5-ylsulfanyl)-acetic acid ethyl, Boc deprotection, reaction with dimethylsulfamoyl chloride and hydrolysis of the ester moiety as described in general procedure (I) gave the title compound.

Sources & evidence

ORD record: ord-63b41943e9f147ab82a5c2a46c989920
Source dataset: uspto-grants-2009_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07582769B2

Reaction notes

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