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

HRID 1972860Notes

Reaction equation

HRID 1972860 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.[CH2:35]([N:37]1[CH2:42][CH2:41][NH:40][CH2:39][CH2:38]1)[CH3:36]>>[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:40]5[CH2:41][CH2:42][N:37]([CH2:35][CH3:36])[CH2:38][CH2:39]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 791961-EthylpiperazineHCID 693032915-(2-benzyl-2H-indazol-6-yl)-7-(4-bromomethyl-phenyl)-pyrrolo[2,1-f][1,2,4]triazin-4-ylamine

Product 1

HCID 585299195-(2-Benzyl-2H-indazol-6-yl)-7-[4-(4-ethyl-piperazin-1-ylmethyl)-phenyl]-pyrrolo[2,1-f][1,2,4]triazin-4-ylamineYield 1.2%

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-ethyl-piperazine as starting materials, 3.4 mg (1.2%) 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), 2.40-2.20 (m, 10), 1.0 (t, 3 H); ES-MS m/z 543.01 [M+H]+, HPLC RT (min) 2.28.

Sources & evidence

ORD record
ord-120f9ca80c6d4a8a94faac9c138eef5e
Source dataset
uspto-grants-2013_04
Patent number
US08431695B2

Reaction notes

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