Cyclopentanone → HCID 58529485, compound

HRID 1972849Notes

Reaction equation

[NH2:1][CH2:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[N:17]3[C:12]([C:13]([NH2:18])=[N:14][CH:15]=[N:16]3)=[C:11]([C:19]3[CH:20]=[CH:21][C:22]4[C:26]([CH:27]=3)=[N:25][N:24]([CH2:28][C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)[CH:23]=4)[CH:10]=2)=[CH:5][CH:4]=1.[C:35]1(=O)[CH2:39][CH2:38][CH2:37][CH2:36]1>>[CH2:28]([N:24]1[CH:23]=[C:22]2[C:26]([CH:27]=[C:19]([C:11]3[CH:10]=[C:9]([C:6]4[CH:7]=[CH:8][C:3]([CH2:2][NH:1][CH:35]5[CH2:39][CH2:38][CH2:37][CH2:36]5)=[CH:4][CH:5]=4)[N:17]4[C:12]=3[C:13]([NH2:18])=[N:14][CH:15]=[N:16]4)[CH:20]=[CH:21]2)=[N:25]1)[C:29]1[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=1

Participants

Reactant 2

HCID 8452Cyclopentanone

HCID 58529851HCID 58529851, compound

Product 1

HCID 58529485HCID 58529485, compoundYield 12%

Procedure

Using a procedure similar to that of Example 111 with 7-(4-Aminomethyl-phenyl)-5-(2-benzyl-2H-indazol-6-yl)-pyrrolo[2,1-f][1,2,4]triazin-4-ylamine and cyclopentanone as starting materials, 29.3 mg (12%) of the desired product was isolated. 1H NMR (300 MHz, DMSO-d6) δ 8.80 (s, 1 H), 8.05 (d, 2H), 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), 3.75 (s, 2 H) 3.00 (m, 1 H), 2.80-2.70 (m, 4 H), 2.50-2.40 (m, 4H); ES-MS m/z 514.16 [M+H]+, HPLC RT (min) 2.62.

Sources & evidence

ORD record: ord-219e27eeabc543fe9a56ea826d171890
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08431695B2

Reaction notes

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