Ethylene Oxide → (+/-)-2-(3,3-Difluoro-4-{3-methoxy-4-[7-(2-methoxy-pyridin-3-yl)-pyrrolo[2,1-f][1,2,4]triazin-2-ylamino]-phenyl}-piperidin-1-yl)-ethanol

HRID 60369Notes

Reaction equation

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

Participants

Reactant 2

HCID 6354Ethylene Oxide

HCID 86581723(+/-)-[4-(3,3-Difluoro-piperidin-4-yl)-2-methoxy-phenyl]-[7-(2-methoxy-pyridin-3-yl)-pyrrolo[2,1-f][1,2,4]triazin-2-yl]-amine

Product 1

HCID 86581581(+/-)-2-(3,3-Difluoro-4-{3-methoxy-4-[7-(2-methoxy-pyridin-3-yl)-pyrrolo[2,1-f][1,2,4]triazin-2-ylamino]-phenyl}-piperidin-1-yl)-ethanol

Procedure

Ethylene oxide and (±)-[4-(3,3-difluoro-piperidin-4-yl)-2-methoxy-phenyl]-[7-(2-methoxy-pyridin-3-yl)-pyrrolo[2,1-f][1,2,4]triazin-2-yl]-amine (Example 12, 68 mg) were converted to the title product by a procedure similar to the one described for Example 8 to give a yellow foam (51 mg, 68% yield). 1H NMR (CDCl3): 8.72 (s, 1H), 8.48 (d, J=7.4 Hz, 1H), 8.28 (d, J=8.1 Hz, 1H), 8.24 (d, J=4.3 Hz, 1H), 7.51 (s, 1H), 7.14 (d, J=3.6 Hz, 1H), 7.08 (m, 1H), 6.84 (m, 2H), 4.02 (s, 3H), 3.92 (s, 3H), 3.68 (m, 2H), 3.25 (m, 1H), 3.10 (m, 1H), 2.90 (m, 1H), 2.74 (m, 1H), 2.65 (m, 1H), 2.46 (dd, J=28.3 (F-H vic. coupling), 11.7 Hz, 1H), 2.27 (m, 3H), 1.90 (m, 1H); LC/MS (ESI+): 510.54 (M+H).

Sources & evidence

ORD record: ord-84c6dc1241104597ab8a0ba626b7342a
Source dataset: uspto-grants-2016_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09440984B2

Reaction notes

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