4-(4-Aminobenzyl)thiomorpholine 1,1-dioxide → [4-(1,1-Dioxo-1$1(6)-thiomorpholin-4-ylmethyl)-phenyl]-[7-(6-methoxy-pyridin-3-yl)-pyrrolo[2,1-f][1,2,4]triazin-2-yl]-amine

HRID 1262205Notes

Reaction equation

HRID 1262205 reaction equation
CS([C:4]1[N:9]=[CH:8][C:7]2=[CH:10][CH:11]=[C:12]([C:13]3[CH:14]=[N:15][C:16]([O:19][CH3:20])=[CH:17][CH:18]=3)[N:6]2[N:5]=1)=O.[O:21]=[S:22]1(=[O:36])[CH2:27][CH2:26][N:25]([CH2:28][C:29]2[CH:34]=[CH:33][C:32]([NH2:35])=[CH:31][CH:30]=2)[CH2:24][CH2:23]1>>[O:36]=[S:22]1(=[O:21])[CH2:23][CH2:24][N:25]([CH2:28][C:29]2[CH:34]=[CH:33][C:32]([NH:35][C:4]3[N:9]=[CH:8][C:7]4=[CH:10][CH:11]=[C:12]([C:13]5[CH:14]=[N:15][C:16]([O:19][CH3:20])=[CH:17][CH:18]=5)[N:6]4[N:5]=3)=[CH:31][CH:30]=2)[CH2:26][CH2:27]1

Participants

3

Reactant 2

HCID 27796824-(4-Aminobenzyl)thiomorpholine 1,1-dioxideHCID 667108472-Methanesulfinyl-7-(6-methoxy-pyridin-3-yl)-pyrrolo[2,1-f][1,2,4]triazine

Product 1

HCID 86661689[4-(1,1-Dioxo-1$1(6)-thiomorpholin-4-ylmethyl)-phenyl]-[7-(6-methoxy-pyridin-3-yl)-pyrrolo[2,1-f][1,2,4]triazin-2-yl]-amine

Procedure

[4-(1,1-Dioxo-1$1(6)-thiomorpholin-4-ylmethyl)-phenyl]-[7-(6-methoxy-pyridin-3-yl)-pyrrolo[2,1-f][1,2,4]triazin-2-yl]-amine was prepared from 2-methanesulfinyl-7-(6-methoxy-pyridin-3-yl)-pyrrolo[2,1-f][1,2,4]triazine and 4-(1,1-dioxo-1$1(6)-thiomorpholin-4-ylmethyl)-phenylamine in an analogous manner to Example 1049. Product isolated as a yellow foam (10 mg, 6%). LCMS (m/e) 465 (M+H); 1H-NMR (CDCl3, 400 MHz) δ 8.77 (d, 1H, J=2.1 Hz), 8.72 (s, 1H), 8.40 (dd, 1H, J=8.7 and 2.4 Hz), 7.58 (d, 2H, J=8.4 Hz), 7.26 (d, 2H, J=8.4 Hz), 6.94 (d, 1H, J=4.7 Hz), 6.92-6.84 (m, 2H), 6.82 (s, 1H), 4.04 (s, 3H), 3.62 (s, 2H), 3.10-3.03 (m, 4H), 3.03-2.96 (m, 4H).

Sources & evidence

ORD record
ord-7b6414129b9d460bb32262163d23a6a5
Source dataset
uspto-grants-2013_06
Patent number
US08471005B2

Reaction notes

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