4-Bromo-1-methyl-1H-imidazole → [7-(1-Methyl-1H-imidazol-4-yl)-pyrrolo[2,1-f][1,2,4]triazin-2-yl]-[4-(4-methyl-piperazin-1-yl)-phenyl]-amine

HRID 1262197Notes

Reaction equation

Br[C:2]1[N:3]=[CH:4][N:5]([CH3:7])[CH:6]=1.[CH3:8][N:9]1[CH2:14][CH2:13][N:12]([C:15]2[CH:20]=[CH:19][C:18]([NH:21][C:22]3[N:27]=[CH:26][C:25]4=[CH:28][CH:29]=[C:30](B5OC(C)(C)C(C)(C)O5)[N:24]4[N:23]=3)=[CH:17][CH:16]=2)[CH2:11][CH2:10]1>>[CH3:7][N:5]1[CH:6]=[C:2]([C:30]2[N:24]3[C:25]([CH:26]=[N:27][C:22]([NH:21][C:18]4[CH:19]=[CH:20][C:15]([N:12]5[CH2:13][CH2:14][N:9]([CH3:8])[CH2:10][CH2:11]5)=[CH:16][CH:17]=4)=[N:23]3)=[CH:28][CH:29]=2)[N:3]=[CH:4]1

Participants

Reactant 2

HCID 12776534-Bromo-1-methyl-1H-imidazole

HCID 57416042N-[4-(4-methylpiperazin-1-yl)phenyl]-7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrrolo[2,1-f][1,2,4]triazin-2-amine

Product 1

HCID 66712141[7-(1-Methyl-1H-imidazol-4-yl)-pyrrolo[2,1-f][1,2,4]triazin-2-yl]-[4-(4-methyl-piperazin-1-yl)-phenyl]-amine

Procedure

[7-(1-Methyl-1H-imidazol-4-yl)-pyrrolo[2,1-f][1,2,4]triazin-2-yl]-[4-(4-methyl-piperazin-1-yl)-phenyl]-amine was prepared from 4-bromo-1-methyl-1H-imidazole and [4-(4-methyl-piperazin-1-yl)-phenyl]-[7-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-pyrrolo[2,1-f][1,2,4]triazin-2-yl]-amine in an analogous manner to Example 1042b. Product isolated as a yellow solid (16 mg, 17%). m.p.=200-202° C.; LCMS (m/e) 389 (M+H); 1H-NMR (CDCl3, 400 MHz) δ 8.63 (s, 1H), 7.92 (d, 1H, J=1.3 Hz), 7.57-7.47 (m, 3H), 7.30-7.24 (m, 1H), 7.02-6.96 (m, 2H), 6.81 (d, 1H, J=4.8 Hz), 6.57 (bs, 1H), 3.74 (s, 3H), 3.24-3.18 (m, 4H), 2.66-2.57 (m, 4H), 2.38 (s, 3H).

Sources & evidence

ORD record: ord-8341d89337fd4e2b99c4d3bbf4410416
Source dataset: uspto-grants-2013_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08471005B2

Reaction notes

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