Methyl iodide → HCID 58529642, compound

HRID 1972829Notes

Reaction equation

[CH2:1]1[CH:6]2[CH2:7][NH:8][CH2:9][CH2:10][N:5]2[CH2:4][CH:3]([C:11]2[N:19]3[C:14]([C:15]([NH2:20])=[N:16][CH:17]=[N:18]3)=[C:13]([C:21]3[CH:22]=[CH:23][C:24]4[C:28]([CH:29]=3)=[N:27][N:26]([C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)[CH:25]=4)[CH:12]=2)[O:2]1.I[CH3:37]>>[CH3:37][N:8]1[CH2:9][CH2:10][N:5]2[CH:6]([CH2:1][O:2][CH:3]([C:11]3[N:19]4[C:14]([C:15]([NH2:20])=[N:16][CH:17]=[N:18]4)=[C:13]([C:21]4[CH:22]=[CH:23][C:24]5[C:28]([CH:29]=4)=[N:27][N:26]([C:30]4[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=4)[CH:25]=5)[CH:12]=3)[CH2:4]2)[CH2:7]1

Participants

Reactant 2

HCID 6328Methyl iodide

HCID 58529507HCID 58529507, compound

Product 1

HCID 58529642HCID 58529642, compoundYield 52%

Procedure

In a manner similar to the procedure described for the preparation of Example 103 and using 7-(octahydropyrazino[2,1-c][1,4]oxazin-3-yl)-5-(2-phenyl-2H-indazol-6-yl)pyrrolo[2,1-f][1,2,4]triazin-4-amine and iodomethane as the starting materials, 27 mg (52%) of the desired product was isolated. 1H NMR (300 MHz, DMSO-d6) 9.16 (s, 1 H), 8.10 (d, 2 H), 7.94 (s, 1 H), 7.85 (d, 1 H), 7.68 (s, 1 H), 7.59 (t, 2 H), 7.44 (t, 1 H), 7.21 (dd, 1H), 6.78 (s, 1H), 5.12 (dd, 1H), 3.78 (dd, 1H), 3.39-3.30 (m, 1H), 3.00 (dd, 1H), 2.71-2.67 (m, 2H), 2.61-2.54 (m, 1H), 2.48-2.38 (m, 1H), 2.27-2.19 (m, 2H), 2.15 (s, 3H), 2.10-2.02 (m, 1H), 1.63 (t, 1H); LC-MS [M+H]+=481, RT=1.08 min.

Workup

customIn a manner similar to the procedure described for the preparation of Example 103

Sources & evidence

ORD record: ord-8e65f69209ad4cceb494aabedb9ecf6f
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08431695B2

Reaction notes

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