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

HRID 1262199Notes

Reaction equation

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

Participants

Reactant 2

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

HCID 57416041N-[4-(Morpholin-4-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 66712483[7-(1-Methyl-1H-imidazol-4-yl)-pyrrolo[2,1-f][1,2,4]triazin-2-yl]-(4-morpholin-4-yl-phenyl)-amine

Procedure

[7-(1-Methyl-1H-imidazol-4-yl)-pyrrolo[2,1-f][1,2,4]triazin-2-yl]-(4-morpholin-4-yl-phenyl)-amine was prepared from 4-bromo-1-methyl-1H-imidazole and (4-morpholin-4-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 foam (7 mg, 7%). LCMS (m/e) 376 (M+H); 1H-NMR (CDCl3, 400 MHz) δ 8.64 (s, 1H), 7.92 (d, 1H, J=1.2 Hz), 7.55 (d, 2H, J=8.9 Hz), 5.52 (s, 1H), 7.27 (d, 1H, J=4.8 Hz), 6.97 (d, 2H, J=8.9 Hz), 6.82 (d, 1H, J=4.8 Hz), 6.59 (bs, 1H), 3.93-3.87 (m, 4H), 3.76 (s, 3H), 3.18-3.13 (m, 4H).

Sources & evidence

ORD record: ord-1a0b46bcfa434adc9a4894ff5c05d684
Source dataset: uspto-grants-2013_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08471005B2

Reaction notes

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