Pyridine → HCID 178488811, compound

HRID 985812Notes

Reaction equation

HRID 985812 reaction equation
C1(O[C:8](=[O:27])[NH:9][C:10]2[S:11][C:12]3[C:18]([CH:19]4[CH2:24][O:23][CH2:22][CH2:21][O:20]4)=[CH:17][CH:16]=[C:15]([O:25][CH3:26])[C:13]=3[N:14]=2)C=CC=CC=1.N1C=CC=CC=1.[CH3:34][NH:35][C@@H:36]1[CH2:41][CH2:40][C@H:39]([OH:42])[CH2:38][CH2:37]1>C(Cl)(Cl)Cl>[O:20]1[CH2:21][CH2:22][O:23][CH2:24][CH:19]1[C:18]1[C:12]2[S:11][C:10]([NH:9][C:8](=[O:27])[N:35]([C@H:36]3[CH2:41][CH2:40][C@@H:39]([OH:42])[CH2:38][CH2:37]3)[CH3:34])=[N:14][C:13]=2[C:15]([O:25][CH3:26])=[CH:16][CH:17]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 20769454(+)-(7-[1,4]Dioxan-2-yl-4-methoxy-benzothiazol-2-yl)-carbamic acid phenyl esterHCID 178484842HCID 178484842, compound

Product 1

HCID 178488811HCID 178488811, compoundYield 69%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a stirred solution of 100 mg (0.26 mmol) (+)-(7-[1,4]dioxan-2-yl-4-methoxy-benzothiazol-2-yl)-carbamic acid phenyl ester and 0.06 ml (0.78 mmol) pyridine in 5 ml chloroform at room temperature was added 47 mg (0.36 mmol) cis-4-methylamino-cyclohexanol and stirring continued at 50° C. for 16 h. The reaction mixture was then concentrated in vacuo. Flash chromatography (1/1 acetone/heptane then acetone) followed by trituration in ether and hexane afforded 75 mg (69%) (+)-cis-3-(7-[1,4]dioxan-2-yl-4-methoxy-benzothiazol-2-yl)-1-(4-hydroxy-cyclohexyl)-1-methyl-urea as a white solid. [α]D20=+18.8° (c=1.07, CHCl3), ES-MS m/e (%): 422 (M+H+, 100).

Workup

  1. concentrationThe reaction mixture was then concentrated in vacuo

Sources & evidence

ORD record
ord-55e2baf204de43bc8ed51606122dfed7
Source dataset
uspto-grants-2005_03
Patent number
US06872833B2

Reaction notes

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