1-(Thiazol-2-yl)piperazine → (4-{1-[5-Chloro-2-(trifluoromethyl)benzyl]-1,2,3,4-tetrahydropyrido[2,3-b]pyrazin-7-yl}phenyl)-(4-thiazol-2-yl-piperazin-1-yl)methanone

HRID 2074692Notes

Reaction equation

HRID 2074692 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:28]([F:31])([F:30])[F:29])=[C:6]([CH:27]=1)[CH2:7][N:8]1[CH2:13][CH2:12][NH:11][C:10]2[N:14]=[CH:15][C:16]([C:18]3[CH:26]=[CH:25][C:21]([C:22](O)=[O:23])=[CH:20][CH:19]=3)=[CH:17][C:9]1=2.[S:32]1[CH:36]=[CH:35][N:34]=[C:33]1[N:37]1[CH2:42][CH2:41][NH:40][CH2:39][CH2:38]1>>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:28]([F:30])([F:29])[F:31])=[C:6]([CH:27]=1)[CH2:7][N:8]1[CH2:13][CH2:12][NH:11][C:10]2[N:14]=[CH:15][C:16]([C:18]3[CH:26]=[CH:25][C:21]([C:22]([N:40]4[CH2:41][CH2:42][N:37]([C:33]5[S:32][CH:36]=[CH:35][N:34]=5)[CH2:38][CH2:39]4)=[O:23])=[CH:20][CH:19]=3)=[CH:17][C:9]1=2

Participants

3

Reactant 2

HCID 9118061-(Thiazol-2-yl)piperazineHCID 469067184-{1-[5-Chloro-2-(trifluoromethyl)benzyl]-1,2,3,4-tetrahydropyrido[2,3-b]pyrazin-7-yl}benzoic acid

Product 1

HCID 57886037(4-{1-[5-Chloro-2-(trifluoromethyl)benzyl]-1,2,3,4-tetrahydropyrido[2,3-b]pyrazin-7-yl}phenyl)-(4-thiazol-2-yl-piperazin-1-yl)methanoneYield 61%

Procedure

4-{1-[5-Chloro-2-(trifluoromethyl)benzyl]-1,2,3,4-tetrahydro-pyrido[2,3-b]pyrazin-7-yl}benzoic acid (70 mg) was reacted with 1-thiazol-2-yl-piperazine as in General Procedure 8 to give the title compound as a yellow solid (61% yield). M.p. 243-244, LCMS: m/z=598.92 (M+H+), 1H-NMR (CDCl3, 400 MHz) δ 3.49-3.92 (m, 12H), 4.63 (s, 2H), 5.06 (bs, 1H), 6.57-6.64 (m, 2H), 7.21 (d, J=3.52 Hz, 1H), 7.35-7.43 (m, 5H), 7.51 (s, 1H), 7.65 (d, J=8.4 Hz, 1H), 7.76 (s, 1H).

Sources & evidence

ORD record
ord-8c70567b4f334264bdd7ad196e532070
Source dataset
uspto-grants-2011_04
Patent number
US07919502B2

Reaction notes

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