Quinoline-3-boronic acid → [4-(4-Methyl-piperazin-1-yl)-phenyl]-(7-quinolin-3-yl-pyrrolo[2,1-f][1,2,4]triazin-2-yl)-amine

HRID 1262191Notes

Reaction equation

HRID 1262191 reaction equation
Br[C:2]1[N:10]2[C:5]([CH:6]=[N:7][C:8]([NH:11][C:12]3[CH:17]=[CH:16][C:15]([N:18]4[CH2:23][CH2:22][N:21]([CH3:24])[CH2:20][CH2:19]4)=[CH:14][CH:13]=3)=[N:9]2)=[CH:4][CH:3]=1.[N:25]1[C:34]2[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=2)[CH:28]=[C:27](B(O)O)[CH:26]=1>>[CH3:24][N:21]1[CH2:20][CH2:19][N:18]([C:15]2[CH:16]=[CH:17][C:12]([NH:11][C:8]3[N:7]=[CH:6][C:5]4=[CH:4][CH:3]=[C:2]([C:27]5[CH:26]=[N:25][C:34]6[C:29]([CH:28]=5)=[CH:30][CH:31]=[CH:32][CH:33]=6)[N:10]4[N:9]=3)=[CH:13][CH:14]=2)[CH2:23][CH2:22]1

Participants

3

Reactant 2

HCID 2734663Quinoline-3-boronic acidHCID 66711200(7-Bromo-pyrrolo[2,1-f][1,2,4]triazin-2-yl)-[4-(4-methyl-piperazin-1-yl)-phenyl]-amine

Product 1

HCID 66711340[4-(4-Methyl-piperazin-1-yl)-phenyl]-(7-quinolin-3-yl-pyrrolo[2,1-f][1,2,4]triazin-2-yl)-amine

Procedure

[4-(4-Methyl-piperazin-1-yl)-phenyl]-(7-quinolin-3-yl-pyrrolo[2,1-f][1,2,4]triazin-2-yl)-amine was prepared from (7-bromo-pyrrolo[2,1-f][1,2,4]triazin-2-yl)-[4-(4-methyl-piperazin-1-yl)-phenyl]-amine and 3-quinolineboronic acid in an analogous manner to Example 1031b. Product isolated as a yellow solid (49 mg, 40%). m.p.=235-241° C.; LCMS (m/e) 436 (M+H); 1H-NMR (CDCl3, 400 MHz) δ 9.38 (s, 1H), 9.34 (s, 1H), 8.76 (s, 1H), 8.13 (d, 1H, J=9.1 Hz), 7.85 (d, 1H, J=7.0 Hz), 7.80-7.69 (m, 1H), 7.63-7.52 (m, 3H), 7.25-7.17 (m, 1H), 6.98 (d, 2H, J=7.9 Hz), 6.93-6.86 (m, 1H), 6.70 (s, 1H), 3.29-3.19 (m, 4H), 2.69-2.57 (m, 4H), 2.39 (s, 3H).

Sources & evidence

ORD record
ord-92980adf10d143daa08bffb70f88cc8c
Source dataset
uspto-grants-2013_06
Patent number
US08471005B2

Reaction notes

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