(S)-6-bromo-7-(dimethoxymethyl)-2-methyl-1,2,3,4-tetrahydro-1,8-naphthyridine → (S)-1-((2-(dimethoxymethyl)-7-methyl-5,6,7,8-tetrahydro-1,8-naphthyridin-3-yl)methyl)-4-methylpiperazin-2-one

HRID 1778029Notes

Reaction equation

HRID 1778029 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:9](=[N:10][C:11]=1[CH:12]([O:15][CH3:16])[O:13][CH3:14])[NH:8][C@@H:7]([CH3:17])[CH2:6][CH2:5]2.COC(OC)C1C([CH2:31][N:32]2[CH2:37][CH2:36][N:35]([CH3:38])[CH2:34][C:33]2=[O:39])=CC2CCCNC=2N=1>>[CH3:14][O:13][CH:12]([O:15][CH3:16])[C:11]1[C:2]([CH2:31][N:32]2[CH2:37][CH2:36][N:35]([CH3:38])[CH2:34][C:33]2=[O:39])=[CH:3][C:4]2[CH2:5][CH2:6][C@H:7]([CH3:17])[NH:8][C:9]=2[N:10]=1

Participants

3

Reactant 2

HCID 118036532(S)-6-bromo-7-(dimethoxymethyl)-2-methyl-1,2,3,4-tetrahydro-1,8-naphthyridine2×HCID 1180366581-((2-(Dimethoxymethyl)-5,6,7,8-tetrahydro-1,8-naphthyridin-3-yl)methyl)-4-methylpiperazin-2-one

Product 1

HCID 118036828(S)-1-((2-(dimethoxymethyl)-7-methyl-5,6,7,8-tetrahydro-1,8-naphthyridin-3-yl)methyl)-4-methylpiperazin-2-one

Procedure

From (S)-6-bromo-7-(dimethoxymethyl)-2-methyl-1,2,3,4-tetrahydro-1,8-naphthyridine (intermediate 264 (enantiomer 1)), synthesized in an analogous manner to intermediate 81, the title compound was obtained as a brown solid. (UPLC-MS 6) tR 0.39; ESI-MS 349.2 [M+H]+.

Sources & evidence

ORD record
ord-f405fa7ef9be42a1b5e4654e4e14bb03
Source dataset
uspto-grants-2016_02
Patent number
US09266883B2

Reaction notes

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