1-(5-Chloro-2-trifluoromethylbenzyl)-7-iodo-1,2,3,4-tetrahydropyrido[2,3-b]pyrazine → [4-[1-[[5-Chloro-2-(trifluoromethyl)phenyl]methyl]-1,2,3,4-tetrahydropyrido[2,3-b]pyrazin-7-yl]phenyl][4-(1-pyrrolidinyl)-1-piperidinyl]methanone

HRID 659389Notes

Reaction equation

HRID 659389 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:20]([F:23])([F:22])[F:21])=[C:6]([CH:19]=1)[CH2:7][N:8]1[CH2:13][CH2:12][NH:11][C:10]2[N:14]=[CH:15][C:16](I)=[CH:17][C:9]1=2.[N:24]1([CH:29]2[CH2:34][CH2:33][N:32]([C:35]([C:37]3[CH:42]=[CH:41][C:40](B4OC(C)(C)C(C)(C)O4)=[CH:39][CH:38]=3)=[O:36])[CH2:31][CH2:30]2)[CH2:28][CH2:27][CH2:26][CH2:25]1>>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:20]([F:23])([F:22])[F:21])=[C:6]([CH:19]=1)[CH2:7][N:8]1[CH2:13][CH2:12][NH:11][C:10]2[N:14]=[CH:15][C:16]([C:40]3[CH:41]=[CH:42][C:37]([C:35]([N:32]4[CH2:31][CH2:30][CH:29]([N:24]5[CH2:25][CH2:26][CH2:27][CH2:28]5)[CH2:34][CH2:33]4)=[O:36])=[CH:38][CH:39]=3)=[CH:17][C:9]1=2

Participants

3

Reactant 2

HCID 578860851-(5-Chloro-2-trifluoromethylbenzyl)-7-iodo-1,2,3,4-tetrahydropyrido[2,3-b]pyrazineHCID 57886103[4-(Pyrrolidin-1-yl)piperidin-1-yl][4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]methanone

Product 1

HCID 46871638[4-[1-[[5-Chloro-2-(trifluoromethyl)phenyl]methyl]-1,2,3,4-tetrahydropyrido[2,3-b]pyrazin-7-yl]phenyl][4-(1-pyrrolidinyl)-1-piperidinyl]methanoneYield 19%

Procedure

1-(5-Chloro-2-trifluoromethylbenzyl)-7-iodo-1,2,3,4-tetrahydropyrido[2,3-b]pyrazine (40 mg) was reacted with (4-(pyrrolidin-1-yl)piperidin-1-yl)-[4-(4,4,5,5-tetramethyl[1,3,2]dioxaborolan-2-yl)phenyl]methanone as in General Procedure 4A to give the title compound as an orange foam (19% yield). M.p. (foam), LCMS: m/z=487.19, 1H-NMR (CDCl3, 400 MHz) δ 1.43-1.62 (m, 3H), 1.65-1.99 (m, 3H), 2.21-2.30 (m, 2H), 2.52-2.61 (m, 6H), 2.87-3.08 (m, 3H), 3.47-3.51 (m, 2H), 3.65-3.71 (m, 2H), 4.62 (s, 2H), 5.02 (s, 1H), 6.59 (d, J=1.5 Hz, 1H), 7.31-7.39 (m, 5H), 7.50 (s, 1H), 7.65 (d, J=8.4 Hz, 1H), 7.74 (s, 1H).

Sources & evidence

ORD record
ord-fb5993a5f65a4da8ad6fe83682a1ed3f
Source dataset
uspto-grants-2011_12
Patent number
US08080561B2

Reaction notes

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