4-(4-Chlorophenyl)-1,2,3,6-tetrahydropyridine → (S)-7-((4-(4-chlorophenyl)-5,6-dihydropyridin-1(2H)-yl)methyl)-4-isopropyl-3-methyl-3,4-dihydropyrido[3,2-b]pyrazin-2(1H)-one

HRID 716236Notes

Reaction equation

HRID 716236 reaction equation
O[CH2:2][C:3]1[CH:12]=[N:11][C:10]2[N:9]([CH:13]([CH3:15])[CH3:14])[C@@H:8]([CH3:16])[C:7](=[O:17])[NH:6][C:5]=2[CH:4]=1.[Cl:18][C:19]1[CH:24]=[CH:23][C:22]([C:25]2[CH2:26][CH2:27][NH:28][CH2:29][CH:30]=2)=[CH:21][CH:20]=1>>[Cl:18][C:19]1[CH:24]=[CH:23][C:22]([C:25]2[CH2:30][CH2:29][N:28]([CH2:2][C:3]3[CH:12]=[N:11][C:10]4[N:9]([CH:13]([CH3:15])[CH3:14])[C@@H:8]([CH3:16])[C:7](=[O:17])[NH:6][C:5]=4[CH:4]=3)[CH2:27][CH:26]=2)=[CH:21][CH:20]=1

Participants

3

Reactant 2

HCID 1857174-(4-Chlorophenyl)-1,2,3,6-tetrahydropyridineHCID 66775347(S)-7-(hydroxymethyl)-4-isopropyl-3-methyl-3,4-dihydropyrido[3,2-b]pyrazin-2(1H)-one

Product 1

HCID 58324507(S)-7-((4-(4-chlorophenyl)-5,6-dihydropyridin-1(2H)-yl)methyl)-4-isopropyl-3-methyl-3,4-dihydropyrido[3,2-b]pyrazin-2(1H)-one

Procedure

Compound 60 was prepared using a procedure analogous to that described in connection with compound 1D, except that (S)-7-(hydroxymethyl)-4-isopropyl-3-methyl-3,4-dihydropyrido[3,2-b]pyrazin-2(1H)-one was used instead of (S)-3-(hydroxymethyl)-6a,7,8,9-tetrahydropyrido[3,2-e]pyrrolo[1,2-a]pyrazin-6(5H)-one and 4-(4-chlorophenyl)-1,2,3,6-tetrahydropyridine was used instead of 1-(4-chlorophenyl)piperazine. 1H NMR (CHLOROFORM-d) δ (ppm): 8.33 (s, 1H), 7.84 (d, J=1.8 Hz, 1H), 7.21-7.36 (m, 4H), 7.04 (d, J=1.5 Hz, 1H), 6.06 (br. s., 1H), 4.64-4.84 (m, 1H), 4.28 (q, J=6.7 Hz, 1H), 3.52 (s, 2H), 3.05-3.27 (m, 2H), 2.65-2.79 (m, 2H), 2.54 (br. s., 2H), 1.37 (d, J=6.8 Hz, 3H), 1.25-1.33 (m, 6H); [M+H] calc'd for C23H27ClN4O, 411. found, 411.

Sources & evidence

ORD record
ord-ac71b4ab4d844c70bebb88dea53fc37d
Source dataset
uspto-grants-2015_11
Patent number
US09187497B2

Reaction notes

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