HCID 54153597, compound → HCID 54516126, compound

HRID 1858816Notes

Reaction equation

HRID 1858816 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[CH2:11][O:12][CH:13]1[CH:18]([C:19]2[CH:20]=[N:21][C:22]([CH2:25][CH2:26][N:27]3[C:31]4[CH:32]=[CH:33][CH:34]=[CH:35][C:30]=4[S:29][C:28]3=[S:36])=[CH:23][CH:24]=2)[CH2:17][CH2:16][N:15](C(OC(C)(C)C)=O)[CH2:14]1>[Br-].[Zn+2].[Br-]>[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[CH2:11][O:12][CH:13]1[CH:18]([C:19]2[CH:20]=[N:21][C:22]([CH2:25][CH2:26][N:27]3[C:31]4[CH:32]=[CH:33][CH:34]=[CH:35][C:30]=4[S:29][C:28]3=[S:36])=[CH:23][CH:24]=2)[CH2:17][CH2:16][NH:15][CH2:14]1

Participants

3

Reactant 1

HCID 54153597HCID 54153597, compound

Product 1

HCID 54516126HCID 54516126, compound

Reagents, catalysts & solvents 1

HCID 10421208Zinc bromideCatalyst

Procedure

In an analogous manner to that described in Example 125(h), from tert-butyl (3'RS,4'RS)-3'-(naphthalen-2-ylmethoxy)-6-[2-(2-thioxo-benzothiazol-3-yl)-ethyl]-3',4',5',6'-tetrahydro-2'H-[3,4']bipyridine-1'-carboxylate by cleavage of the BOC group by means of anhydrous zinc bromide there was obtained 3-[2-[(3'RS,4'RS)-3'-(naphthalen-2-ylmethoxy)-1',2',3',4',5',6'-hexahydro-[3,4']bipyridin-6-yl]-ethyl]-3H-benzothiazole-2-thione in the form of an amorphous, colourless solid; MS: 512 (M+H)+.

Sources & evidence

ORD record
ord-b9c5fc7e462a4d5aaa445491222425b4
Source dataset
uspto-grants-2000_11
Patent number
US06150526

Reaction notes

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