Methyl iodide → HCID 58529771, compound

HRID 1972831Notes

Reaction equation

[CH2:1]([N:8]1[C:16]([CH3:17])=[C:15]2[C:10]([CH:11]=[C:12]([C:18]3[CH:19]=[C:20]([CH:28]4[O:33][CH2:32][CH:31]5[CH2:34][NH:35][CH2:36][CH2:37][N:30]5[CH2:29]4)[N:21]4[C:26]=3[C:25]([NH2:27])=[N:24][CH:23]=[N:22]4)[CH:13]=[CH:14]2)=[N:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.I[CH3:39]>>[CH2:1]([N:8]1[C:16]([CH3:17])=[C:15]2[C:10]([CH:11]=[C:12]([C:18]3[CH:19]=[C:20]([CH:28]4[O:33][CH2:32][CH:31]5[CH2:34][N:35]([CH3:39])[CH2:36][CH2:37][N:30]5[CH2:29]4)[N:21]4[C:26]=3[C:25]([NH2:27])=[N:24][CH:23]=[N:22]4)[CH:13]=[CH:14]2)=[N:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Reactant 2

HCID 6328Methyl iodide

HCID 58529487HCID 58529487, compound

Product 1

HCID 58529771HCID 58529771, compoundYield 27%

Procedure

In a manner similar to the procedure described for the preparation of Example 103 and using 5-(2-benzyl-3-methyl-2H-indazol-6-yl)-7-(octahydropyrazino[2,1-c][1,4]oxazin-3-yl)pyrrolo[2,1-f][1,2,4]triazin-4-amine and iodomethane as the starting materials, 18 mg (27%) of the desired product was isolated. 1H NMR (300 MHz, DMSO-d6) 7.91 (s, 1 H), 7.75 (d, 1 H), 7.52 (s, 1 H), 7.34-7.19 (m, 5 H), 7.06 (dd, 1H), 6.72 (s, 1H), 5.63 (s, 2H), 5.14-5.10 (m, 1H), 3.73 (dd, 1H), 3.37-3.30 (m, 1H), 2.93 (dd; 1H), 2.75-2.63 (m, 4H), 2.61 (s, 3H), 2.41 (t, 1H), 2.25-2.06 (m, 3H), 1.57 (s, 3H); LC-MS [M+H]+=509, RT=0.28 min.

Workup

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

Sources & evidence

ORD record: ord-aa269f89acac41c89eb022bc0725ac7f
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08431695B2

Reaction notes

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