N-[2-(2-M ethanesulfinyl-pyrrolo[2,1-f][1,2,4]triazin-7-yl)-phenyl]-N-methyl-methanesulfonamide → HCID 66711643, compound

HRID 1262163Notes

Reaction equation

HRID 1262163 reaction equation
[CH3:1][O:2][C:3]1[CH:18]=[C:17]2[C:6]([CH2:7][CH2:8][C:9]3([O:16]2)[CH2:14][CH2:13][N:12]([CH3:15])[CH2:11][CH2:10]3)=[CH:5][C:4]=1[NH2:19].CS([C:23]1[N:28]=[CH:27][C:26]2=[CH:29][CH:30]=[C:31]([C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][C:33]=3[N:38]([CH3:43])[S:39]([CH3:42])(=[O:41])=[O:40])[N:25]2[N:24]=1)=O>>[CH3:1][O:2][C:3]1[CH:18]=[C:17]2[C:6]([CH2:7][CH2:8][C:9]3([O:16]2)[CH2:10][CH2:11][N:12]([CH3:15])[CH2:13][CH2:14]3)=[CH:5][C:4]=1[NH:19][C:23]1[N:28]=[CH:27][C:26]2=[CH:29][CH:30]=[C:31]([C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][C:33]=3[N:38]([CH3:43])[S:39]([CH3:42])(=[O:41])=[O:40])[N:25]2[N:24]=1

Participants

3

Reactant 2

HCID 54577677N-[2-(2-M ethanesulfinyl-pyrrolo[2,1-f][1,2,4]triazin-7-yl)-phenyl]-N-methyl-methanesulfonamideHCID 66712137HCID 66712137, compound

Product 1

HCID 66711643HCID 66711643, compoundYield 18%

Procedure

Following a procedure analogous to 251c, 7-methoxy-1′-methyl-3,4-dihydrospiro[chromene-2,4′-piperidin]-6-amine (0.15 g, 57 mmol) and N-[2-(2-Methanesulfinyl-pyrrolo[2,1-f][1,2,4]triazin-7-yl)-phenyl]-N-methyl-methanesulfonamide (69 mg, 19 mmol) were converted to the title compound (23 mgs, 18%) isolated as a TFA salt. H-NMR (DMSO-d6) δ 9.49 (broad s, 1H), 8.92 (s, 1H), 7.94 (s, 1H), 7.65 (s, 2H), 7.69-7.66 (m, 3H), 6.98-6.94 (m, 2H), 6.52 (s, 1H), 3.80 (s, 3H), 3.39-3.31 (m, 2H), 3.23-3.13 (m, 2H), 3.06 (s, 3H), 2.87-2.81 (m, 7H), 2.55-2.51 (m, 2H), 2.00-1.91 (m, 2H), 1.84-1.76 (m, 32H); LC/MS (ESI+): 563.17 (M+H).

Sources & evidence

ORD record
ord-0c709ef0ce0545249a5754ebcc7da2e7
Source dataset
uspto-grants-2013_06
Patent number
US08471005B2

Reaction notes

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