1-Methylpiperazine → 5-(2-Benzyl-2H-indazol-6-yl)-7-[4-(4-methyl-piperazin-1-ylmethyl)-phenyl]-pyrrolo[2,1-f][1,2,4]triazin-4-ylamine

HRID 1972858Notes

Reaction equation

HRID 1972858 reaction equation
[CH2:1]([N:8]1[CH:16]=[C:15]2[C:10]([CH:11]=[C:12]([C:17]3[CH:18]=[C:19]([C:27]4[CH:32]=[CH:31][C:30]([CH2:33]Br)=[CH:29][CH:28]=4)[N:20]4[C:25]=3[C:24]([NH2:26])=[N:23][CH:22]=[N:21]4)[CH:13]=[CH:14]2)=[N:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:35][N:36]1[CH2:41][CH2:40][NH:39][CH2:38][CH2:37]1>>[CH2:1]([N:8]1[CH:16]=[C:15]2[C:10]([CH:11]=[C:12]([C:17]3[CH:18]=[C:19]([C:27]4[CH:32]=[CH:31][C:30]([CH2:33][N:39]5[CH2:40][CH2:41][N:36]([CH3:35])[CH2:37][CH2:38]5)=[CH:29][CH:28]=4)[N:20]4[C:25]=3[C:24]([NH2:26])=[N:23][CH:22]=[N:21]4)[CH:13]=[CH:14]2)=[N:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 531671-MethylpiperazineHCID 693032915-(2-benzyl-2H-indazol-6-yl)-7-(4-bromomethyl-phenyl)-pyrrolo[2,1-f][1,2,4]triazin-4-ylamine

Product 1

HCID 585296715-(2-Benzyl-2H-indazol-6-yl)-7-[4-(4-methyl-piperazin-1-ylmethyl)-phenyl]-pyrrolo[2,1-f][1,2,4]triazin-4-ylamineYield 10%

Procedure

Using a procedure similar to that of Example 282 (step 2) with 5-(2-benzyl-2H-indazol-6-yl)-7-(4-bromomethyl-phenyl)-pyrrolo[2,1-f][1,2,4]triazin-4-ylamine and 1-methyl-piperazine as starting materials, 25 mg (10%) of the desired product was isolated. 1H NMR (300 MHz, DMSO-d6) δ 8.80 (s, 1 H), 8.05 (d, 2 H), 8.00 (s, 1 H), 7.90 (d, 1 H), 7.70 (s, 1 H), 7.60-7.40 (m, 7 H), 7.25 (d, 1 H), 7.20 (s, 1 H), 5.70 (s, 2 H), 3.50 (s, 2 H), 2.50 (m, 4 H), 2.30 (s, 4 H), 2.10 (s, 3 H); ES-MS m/z 529.05 [M+H]+, HPLC RT (min) 2.27.

Sources & evidence

ORD record
ord-a723aef26ed6490b99e1379b00504dd7
Source dataset
uspto-grants-2013_04
Patent number
US08431695B2

Reaction notes

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