Dimethylformamide → (Dimethylamino)-N,N-dimethyl(3H-(1,2,3)triazolo(4,5-b)pyridin-3-yloxy)methaniminium

HRID 2374876Notes

Reaction equation

HRID 2374876 reaction equation
[NH2:1][CH:2]([C:4]1[N:9]=[N:8][C:7]([NH:10][C:11]2[CH:16]=[C:15]([O:17][CH3:18])[C:14]([O:19][CH3:20])=[C:13]([O:21][CH3:22])[CH:12]=2)=[N:6][CH:5]=1)[CH3:3].[F:23][C:24]([F:38])([F:37])[C:25]([NH:27][C:28]1[CH:36]=[CH:35][CH:34]=[CH:33][C:29]=1[C:30](O)=[O:31])=[O:26].C([N:41](CC)CC)C.[CH3:46][N:47]([CH3:50])[CH:48]=[O:49]>>[N:8]1([O:49][C:48]([N:27]([CH3:28])[CH3:25])=[N+:47]([CH3:50])[CH3:46])[C:7]2[N:10]=[CH:11][CH:16]=[CH:15][C:14]=2[N:41]=[N:9]1.[F:23][C:24]([F:37])([F:38])[C:25]([NH:27][C:28]1[CH:36]=[CH:35][CH:34]=[CH:33][C:29]=1[C:30]([NH:1][CH:2]([C:4]1[N:9]=[N:8][C:7]([NH:10][C:11]2[CH:12]=[C:13]([O:21][CH3:22])[C:14]([O:19][CH3:20])=[C:15]([O:17][CH3:18])[CH:16]=2)=[N:6][CH:5]=1)[CH3:3])=[O:31])=[O:26]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 2569212-[(2,2,2-trifluoroacetyl)amino]benzoic acidHCID 534044296-(1-aminoethyl)-N-(3,4,5-trimethoxyphenyl)-1,2,4-triazin-3-amine2×

Product 2

HCID 4641409(Dimethylamino)-N,N-dimethyl(3H-(1,2,3)triazolo(4,5-b)pyridin-3-yloxy)methaniminiumHCID 58711991HCID 58711991, compound

Procedure

In a similar manner as described for Intermediate 18 (below), 6-(1-aminoethyl)-N-(3,4,5-trimethoxyphenyl)-1,2,4-triazin-3-amine (Intermediate 9) (0.10 g, 0.33 mmol), 2-[(trifluoroacetyl)amino]benzoic acid (0.084 g, 0.36 mmol), O-(7-azabenzotriazol-1-yl-N,N,N′,N′-tetramethyluronium hexafluorophospahte (0.14 g, 0.36 mmol) and triethylamine (0.10 mL, 0.73 mmol) in N,N-dimethylformamide (2.0 mL) gave 2-[(trifluoroacetyl)amino]-N-(1-{3-[(3,4,5-trimethoxyphenyl)amino]-1,2,4-triazin-6-yl}ethyl)benzamide (0.12 g) as a white solid. MS m/z 521 (M+1).

Sources & evidence

ORD record
ord-339421a764314a9397ec2e7db10e7a24
Source dataset
uspto-grants-2008_12
Patent number
US07462614B2

Reaction notes

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