3-Aminocyclopentanol → 1-{4-[4-Amino-5-(2-benzyl-2H-indazol-6-yl)-pyrrolo[2,1-f][1,2,4]triazin-7-yl]-benzyl}-pyrrolidin-3-ol

HRID 1972852Notes

Reaction equation

HRID 1972852 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.[NH2:35][CH:36]1C[CH2:39][CH:38]([OH:41])[CH2:37]1>>[NH2:26][C:24]1[C:25]2=[C:17]([C:12]3[CH:13]=[CH:14][C:15]4[C:10]([CH:11]=3)=[N:9][N:8]([CH2:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)[CH:16]=4)[CH:18]=[C:19]([C:27]3[CH:28]=[CH:29][C:30]([CH2:33][N:35]4[CH2:36][CH2:37][CH:38]([OH:41])[CH2:39]4)=[CH:31][CH:32]=3)[N:20]2[N:21]=[CH:22][N:23]=1

Participants

3

Reactant 2

HCID 142993103-AminocyclopentanolHCID 693032915-(2-benzyl-2H-indazol-6-yl)-7-(4-bromomethyl-phenyl)-pyrrolo[2,1-f][1,2,4]triazin-4-ylamine

Product 1

HCID 585294301-{4-[4-Amino-5-(2-benzyl-2H-indazol-6-yl)-pyrrolo[2,1-f][1,2,4]triazin-7-yl]-benzyl}-pyrrolidin-3-olYield 4%

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 3-amino-cyclopentanol as starting materials, 8.7 mg (4%) 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), 4.65 (s, 1 H), 3.60 (m, 2 H), 2.85-2.20 (m, 6 H); ES-MS m/z 515.99 [M+H]+, HPLC RT (min) 2.24.

Sources & evidence

ORD record
ord-279b26baabde4106b3b823d74d4664ef
Source dataset
uspto-grants-2013_04
Patent number
US08431695B2

Reaction notes

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