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

HRID 1972864Notes

Reaction equation

HRID 1972864 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.[NH:35]1[CH2:40][CH2:39][O:38][CH2:37][CH2:36]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:35]5[CH2:40][CH2:39][O:38][CH2:37][CH2:36]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 8083MorpholineHCID 693032915-(2-benzyl-2H-indazol-6-yl)-7-(4-bromomethyl-phenyl)-pyrrolo[2,1-f][1,2,4]triazin-4-ylamine

Product 1

HCID 585297975-(2-Benzyl-2H-indazol-6-yl)-7-(4-morpholin-4-ylmethyl-phenyl)-pyrrolo[2,1-f][1,2,4]triazin-4-ylamineYield 28%

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 morpholine as starting material, 55 mg (28%) of the desired product was isolated. 1H NMR (300 MHz, DMSO-d6) δ 8.80 (s, 1 H), 8.05 (d, 2 H), 8.0 (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), 3.60 (t, 4 H), 3.50 (s 2 H), 2.405 (t, 4 H); ES-MS m/z 516.25 [M+H]+, HPLC RT (min) 2.61.

Sources & evidence

ORD record
ord-c9d56f8a745f4744a09813faaa2f6930
Source dataset
uspto-grants-2013_04
Patent number
US08431695B2

Reaction notes

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