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

HRID 420869Notes

Reaction equation

HRID 420869 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:8](=[CH:9][C:10]=1[O:11][CH3:12])[C@@H:7]([CH:13]=O)[CH2:6]2.[CH3:15][O:16][C:17]1[C:33]([O:34][CH3:35])=[CH:32][C:20]2[CH2:21][C:22](=[O:31])[N:23]([CH2:26][CH2:27][CH2:28][NH:29][CH3:30])[CH2:24][CH2:25][C:19]=2[CH:18]=1>>[CH3:30][N:29]([CH2:13][C@@H:7]1[C:8]2[CH:9]=[C:10]([O:11][CH3:12])[C:3]([O:2][CH3:1])=[CH:4][C:5]=2[CH2:6]1)[CH2:28][CH2:27][CH2:26][N:23]1[C:22](=[O:31])[CH2:21][C:20]2[C:19](=[CH:18][C:17]([O:16][CH3:15])=[C:33]([O:34][CH3:35])[CH:32]=2)[CH2:25][CH2:24]1

Participants

3

Reactant 2

HCID 100172197,8-Dimethoxy-3-[3-(methylamino)propyl]-1,3,4,5-tetrahydro-2H-3-benzazepin-2-oneHCID 87093223(75)-3,4-Dimethoxy-bicyclo[4.2.0]octa-1,3,5-triene-7-carbaldehyde

Product 1

HCID 132999Ivabradine

Procedure

By proceeding as in Example 5, starting from (75)-3,4-dimethoxy-bicyclo[4.2.0]octa-1,3,5-triene-7-carbaldehyde and 7,8-dimethoxy-3-[3-(methylamino)propyl]-1,3,4,5-tetrahydro-2H-3-benzazepin-2-one, ivabradine base is obtained, 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-45b6a3a1be8a41918b0d28e437a0ba5e
Source dataset
uspto-grants-2012_01
Patent number
US08097720B2

Reaction notes

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