N-[2-(2-M ethanesulfinyl-pyrrolo[2,1-f][1,2,4]triazin-7-yl)-phenyl]-N-methyl-methanesulfonamide → HCID 66711696, compound

HRID 1262162Notes

Reaction equation

HRID 1262162 reaction equation
[CH2:1]([N:3]1[CH2:8][CH2:7][O:6][CH:5]([C:9]2[CH:14]=[CH:13][C:12]([NH2:15])=[CH:11][CH:10]=2)[CH2:4]1)[CH3:2].CS([C:19]1[N:24]=[CH:23][C:22]2=[CH:25][CH:26]=[C:27]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=3[N:34]([CH3:39])[S:35]([CH3:38])(=[O:37])=[O:36])[N:21]2[N:20]=1)=O>>[CH2:1]([N:3]1[CH2:8][CH2:7][O:6][CH:5]([C:9]2[CH:14]=[CH:13][C:12]([NH:15][C:19]3[N:24]=[CH:23][C:22]4=[CH:25][CH:26]=[C:27]([C:28]5[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=5[N:34]([CH3:39])[S:35]([CH3:38])(=[O:37])=[O:36])[N:21]4[N:20]=3)=[CH:11][CH:10]=2)[CH2:4]1)[CH3:2]

Participants

3

Reactant 2

HCID 54577677N-[2-(2-M ethanesulfinyl-pyrrolo[2,1-f][1,2,4]triazin-7-yl)-phenyl]-N-methyl-methanesulfonamideHCID 574160684-(4-Ethylmorpholin-2-yl)aniline

Product 1

HCID 66711696HCID 66711696, compoundYield 22%

Procedure

Following a procedure analogous to 251c, 4-(4-Ethyl-morpholin-2-yl)-phenylamine (0.16 g, 78 mmol) and N-[2-(2-Methanesulfinyl-pyrrolo[2,1-f][1,2,4]triazin-7-yl)-phenyl]-N-methyl-methanesulfonamide (94 mg, 26 mmol) were converted to the title compound (35 mgs, 22%) isolated as a TFA salt. H-NMR (DMSO-d6) δ 9.89 (broad s, 1H), 9.56 (s, 1H), 9.00 (s, 1H), 7.79 (d, J=3.3 Hz, 1H), 7.69-7.66 (m, 3H), 7.59-7.58 (m, 2H), 7.20 (d, J=7.8 Hz, 2H), 6.99 (d, J=7.8 Hz, 2H), 4.63 (d, J=11.1 Hz, 1H), 4.18 (d, J=12.9 Hz, 1H), 3.85 (t, J=8.3 Hz, 1H), 3.59-3.32 (m, 2H), 3.12-2.98 (m, 4H), 2.86 (s, 3H), 1.25 (t, J=7.8 Hz, 3H); LC/MS (ESI+): 507.1 (M+H).

Sources & evidence

ORD record
ord-e02f88a602464ebebaae09f47aecf8d4
Source dataset
uspto-grants-2013_06
Patent number
US08471005B2

Reaction notes

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