7,8-Dimethoxy-3-[3-(methylamino)propyl]-1,3,4,5-tetrahydro-2H-3-benzazepin-2-one → Ivabradine

HRID 1963800Notes

Reaction equation

HRID 1963800 reaction equation
CS(O[CH2:6][C@H:7]1[CH2:14][C:13]2[C:8]1=[CH:9][C:10]([O:17][CH3:18])=[C:11]([O:15][CH3:16])[CH:12]=2)(=O)=O.[CH3:19][O:20][C:21]1[C:37]([O:38][CH3:39])=[CH:36][C:24]2[CH2:25][C:26](=[O:35])[N:27]([CH2:30][CH2:31][CH2:32][NH:33][CH3:34])[CH2:28][CH2:29][C:23]=2[CH:22]=1>>[CH3:34][N:33]([CH2:6][C@@H:7]1[C:8]2[CH:9]=[C:10]([O:17][CH3:18])[C:11]([O:15][CH3:16])=[CH:12][C:13]=2[CH2:14]1)[CH2:32][CH2:31][CH2:30][N:27]1[C:26](=[O:35])[CH2:25][C:24]2[C:23](=[CH:22][C:21]([O:20][CH3:19])=[C:37]([O:38][CH3:39])[CH:36]=2)[CH2:29][CH2:28]1

Participants

3

Reactant 2

HCID 100172197,8-Dimethoxy-3-[3-(methylamino)propyl]-1,3,4,5-tetrahydro-2H-3-benzazepin-2-oneHCID 86659917(7S)-(3,4-dimethoxybicyclo[4.2.0]octa-1,3,5-trien-7-yl)methyl methanesulphonate

Product 1

HCID 132999Ivabradine

Procedure

By proceeding as in Example 5, starting from (7S)-(iodomethyl)-3,4-dimethoxybicyclo[4.2.0]octa-1,3,5-triene (or from (7S)-(3,4-dimethoxybicyclo[4.2.0]octa-1,3,5-trien-7-yl)methyl methanesulphonate) and from 7,8-dimethoxy-3-[3-(methylamino)-propyl]-1,3,4,5-tetrahydro-2H-3-benzazepin-2-one, there is obtained ivabradine base, which is then converted into its hydrochloride by following the procedure described in patent specification EP 0 534 859 (Example 2, Step E).

Sources & evidence

ORD record
ord-41f2086f141e4e32b31fe1e90cc218ac
Source dataset
uspto-grants-2013_04
Patent number
US08415468B2

Reaction notes

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