1-Methylindole-3-carboxylic acid → 1-methyl-N-[1-(3-{[4-(methyloxy)phenyl]amino)-1,2,4-triazin-6-yl)ethyl]-1H-indole-3-carboxamide

HRID 2374980Notes

Reaction equation

HRID 2374980 reaction equation
COC1C=CC(NC2N=NC(C(NC(C3CCOCC3)=O)C)=CN=2)=CC=1.[NH2:27][CH:28]([C:30]1[N:35]=[N:34][C:33]([NH:36][C:37]2[CH:42]=[CH:41][C:40]([O:43][CH3:44])=[CH:39][CH:38]=2)=[N:32][CH:31]=1)[CH3:29].[CH3:45][N:46]1[C:54]2[C:49](=[CH:50][CH:51]=[CH:52][CH:53]=2)[C:48]([C:55](O)=[O:56])=[CH:47]1>>[CH3:45][N:46]1[C:54]2[C:49](=[CH:50][CH:51]=[CH:52][CH:53]=2)[C:48]([C:55]([NH:27][CH:28]([C:30]2[N:35]=[N:34][C:33]([NH:36][C:37]3[CH:42]=[CH:41][C:40]([O:43][CH3:44])=[CH:39][CH:38]=3)=[N:32][CH:31]=2)[CH3:29])=[O:56])=[CH:47]1

Participants

4

Reactant 3

HCID 8540401-Methylindole-3-carboxylic acidHCID 58711939N-[1-(3-{[4-(methyloxy)phenyl]amino}-1,2,4-triazin-6-yl)ethyl]tetrahydro-2H-pyran-4-carboxamideHCID 587119996-(1-aminoethyl)-N-[4-(methyloxy)phenyl]-1,2,4-triazin-3-amine2×

Product 1

HCID 587119291-methyl-N-[1-(3-{[4-(methyloxy)phenyl]amino)-1,2,4-triazin-6-yl)ethyl]-1H-indole-3-carboxamideYield 64.8%

Procedure

In a similar manner as described for Intermediate 50, using 6-(1-aminoethyl)-N-[4-(methyloxy)phenyl]-1,2,4-triazin-3-amine (Intermediate 47) (100 mg, 0.41 mmol), and 1-methyl-1h-indole-3-carboxylic acid (79 mg, 0.45 mmol) to give 1-methyl-N-[1-(3-{[4-(methyloxy)phenyl]amino}-1,2,4-triazin-6-yl)ethyl]-1H-indole-3-carboxamide (107 mg) as a yellow solid. MS m/z 403 (M+1).

Sources & evidence

ORD record
ord-213c36396ee447769710e3feaba67bb0
Source dataset
uspto-grants-2008_12
Patent number
US07462614B2

Reaction notes

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