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

HRID 2077858Notes

Reaction equation

HRID 2077858 reaction equation
[CH2:1]([N:3]1[C@@H:8]([CH3:9])[C:7](=[O:10])[NH:6][C:5]2[CH:11]=[C:12]([CH2:15]O)[CH:13]=[N:14][C:4]1=2)[CH3:2].[Cl:17][C:18]1[CH:23]=[CH:22][C:21]([C:24]2[CH2:25][CH2:26][NH:27][CH2:28][CH:29]=2)=[CH:20][CH:19]=1>>[Cl:17][C:18]1[CH:23]=[CH:22][C:21]([C:24]2[CH2:29][CH2:28][N:27]([CH2:15][C:12]3[CH:13]=[N:14][C:4]4[N:3]([CH2:1][CH3:2])[C@@H:8]([CH3:9])[C:7](=[O:10])[NH:6][C:5]=4[CH:11]=3)[CH2:26][CH:25]=2)=[CH:20][CH:19]=1

Participants

3

Reactant 2

HCID 1857174-(4-Chlorophenyl)-1,2,3,6-tetrahydropyridineHCID 59416802(S)-4-ethyl-7-(hydroxymethyl)-3-methyl-3,4-dihydropyrido[2,3-b]pyrazin-2(1H)-one

Product 1

HCID 58324433(S)-7-((4-(4-chlorophenyl)-5,6-dihydropyridin-1(2H)-yl)methyl)-4-ethyl-3-methyl-3,4-dihydropyrido[3,2-b]pyrazin-2(1H)-one

Procedure

Compound 63 was prepared using a procedure analogous to that described in connection with compound 1D, except that (5)-4-ethyl-7-(hydroxymethyl)-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): 7.79 (d, J=1.5 Hz, 1H), 7.68 (br. s., 1H), 7.27-7.34 (m, 4H), 7.02 (s, 1H), 6.06 (br. s., 1H), 4.21 (q, J=6.8 Hz, 1H), 3.98-4.12 (m, 1H), 3.44-3.61 (m, 2H), 3.07-3.26 (m, 3H), 2.75 (t, J=5.2 Hz, 2H), 2.55 (br. s., 2H), 1.36 (d, J=6.8 Hz, 3H), 1.26 (t, J=7.2 Hz, 3H); [M+H] calc'd for C22H25ClN4O, 397; found, 397.

Sources & evidence

ORD record
ord-e6eab2c2ef49416e9624c30b9dd05e31
Source dataset
uspto-grants-2011_04
Patent number
US07928105B2

Reaction notes

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