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

HRID 2374888Notes

Reaction equation

HRID 2374888 reaction equation
BrC1C=C(C=CC=1)C(NC(C1[N:15]=[N:14][C:13]([NH:16][C:17]2[CH:22]=[C:21](OC)[C:20](OC)=C(OC)C=2)=NC=1)C)=O.[NH2:32][CH:33]([C:35]1[N:40]=[N:39][C:38]([NH:41][C:42]2[CH:47]=[C:46]([O:48][CH3:49])[C:45]([O:50][CH3:51])=[C:44]([O:52][CH3:53])[CH:43]=2)=[N:37][CH:36]=1)[CH3:34].[Br:54][C:55]1[S:59][C:58]([C:60](O)=[O:61])=[CH:57][CH:56]=1.C([N:65](CC)CC)C.[CH3:70][N:71]([CH3:74])[CH:72]=[O:73]>>[N:14]1([O:73][C:72]([N:37]([CH3:38])[CH3:36])=[N+:71]([CH3:74])[CH3:70])[C:13]2[N:16]=[CH:17][CH:22]=[CH:21][C:20]=2[N:65]=[N:15]1.[Br:54][C:55]1[S:59][C:58]([C:60]([NH:32][CH:33]([C:35]2[N:40]=[N:39][C:38]([NH:41][C:42]3[CH:43]=[C:44]([O:52][CH3:53])[C:45]([O:50][CH3:51])=[C:46]([O:48][CH3:49])[CH:47]=3)=[N:37][CH:36]=2)[CH3:34])=[O:61])=[CH:57][CH:56]=1

Participants

7

Reactant 5

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 3491155-Bromothiophene-2-carboxylic acidHCID 534044296-(1-aminoethyl)-N-(3,4,5-trimethoxyphenyl)-1,2,4-triazin-3-amine2×HCID 587119543-bromo-N-(1-{3-[(3,4,5-trimethoxyphenyl)amino]-1,2,4-triazin-6-yl}ethyl)benzamide

Product 2

HCID 4641409(Dimethylamino)-N,N-dimethyl(3H-(1,2,3)triazolo(4,5-b)pyridin-3-yloxy)methaniminiumHCID 58711971HCID 58711971, compound

Procedure

In a similar manner as described for Intermediate 18, 6-(1-aminoethyl)-N-(3,4,5-trimethoxyphenyl)-1,2,4-triazin-3-amine (Intermediate 9) (0.20 g, 0.67 mmol), 5-bromothiophene-2-carboxylic acid (0.15 g, 0.73 mmol), O-(7-azabenzotriazol-1-yl-N,N,N′,N′tetramethyluronium hexafluorophospahte (0.28 g, 0.73 mmol) and triethylamine (0.20 mL, 1.4 mmol) in N,N-dimethylformamide (10 mL) gave 5-bromo-N-(1-{3-[(3,4,5-trimethoxyphenyl)amino]-1,2,4-triazin-6-yl}ethyl)thiophene-2-carboxamide (0.35 g) as a white solid. MS m/z 494, 496 (M+1, M+3).

Sources & evidence

ORD record
ord-0e1031e129284827b501ab01e3641a90
Source dataset
uspto-grants-2008_12
Patent number
US07462614B2

Reaction notes

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