Phenyl chloroformate → 3-(4-Methoxy-7-morpholin-4-yl-benzothiazol-2-yl)-1-methyl-1-(4-trifluoromethyl-cyclohexyl)-urea

HRID 1181186Notes

Reaction equation

COC1C2N=C(N)SC=2C([N:13]2[CH2:18][CH2:17][O:16][CH2:15][CH2:14]2)=CC=1.ClC(OC1C=CC=CC=1)=O.C(O[C:37](=[O:56])[NH:38][C:39]1[S:40][C:41]2[C:47](C3C=CC=CC=3)=[CH:46][CH:45]=[C:44]([O:54][CH3:55])[C:42]=2[N:43]=1)C1C=CC=CC=1.[CH3:57][NH:58][CH:59]1[CH2:64][CH2:63][CH:62]([C:65]([F:68])([F:67])[F:66])[CH2:61][CH2:60]1>>[CH3:55][O:54][C:44]1[C:42]2[N:43]=[C:39]([NH:38][C:37](=[O:56])[N:58]([CH3:57])[CH:59]3[CH2:60][CH2:61][CH:62]([C:65]([F:66])([F:67])[F:68])[CH2:63][CH2:64]3)[S:40][C:41]=2[C:47]([N:13]2[CH2:18][CH2:17][O:16][CH2:15][CH2:14]2)=[CH:46][CH:45]=1

Participants

Reactant 4

HCID 15891Phenyl chloroformate

HCID 114028614-Methoxy-7-morpholinobenzo[d]thiazol-2-amine

HCID 11506560N-methyl-4-(trifluoromethyl)cyclohexan-1-amine

HCID 86584926(4-Methoxy-7-phenyl-benzothiazol-2-yl)-carbamic acid benzyl ester

Product 1

HCID 113973103-(4-Methoxy-7-morpholin-4-yl-benzothiazol-2-yl)-1-methyl-1-(4-trifluoromethyl-cyclohexyl)-ureaYield 96%

Procedure

4-Methoxy-7-morpholin-4-yl-benzothiazol-2-ylamine was first reacted with phenyl chloroformate as described for (4-methoxy-7-phenyl-benzothiazol-2-yl)-carbamic acid benzyl ester in WO01/97786 and then with methyl-(4-trifluoromethyl-cyclohexyl)-amine. Usual workup, flash-chromatography (silica, eluent dichloromethane/methanol) and final evaporation of the solvent afforded the title compound as white crystals (96% yield), mp 157-167° C. MS: m/e=473(M+H+). Following the general method of example 1 the compounds of examples 2 to 12 were prepared.

Workup

customUsual workup, flash-chromatography (silica, eluent dichloromethane/methanol) and final evaporation of the solvent

Sources & evidence

ORD record: ord-b9815d7ee0374921b8684edf86176d09
Source dataset: uspto-grants-2007_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07285548B2

Reaction notes

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