2-Chlorobenzoic Acid → 2-chloro-N-(1-(3-{[4-(methyloxy)phenyl]amino}-1,2,4-triazin-6-yl)ethyl]benzamide

HRID 2374978Notes

Reaction equation

HRID 2374978 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].[Cl:45][C:46]1[CH:54]=[CH:53][CH:52]=[CH:51][C:47]=1[C:48](O)=[O:49]>>[Cl:45][C:46]1[CH:54]=[CH:53][CH:52]=[CH:51][C:47]=1[C:48]([NH: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])=[O:49]

Participants

4

Reactant 3

HCID 83742-Chlorobenzoic 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 587119932-chloro-N-(1-(3-{[4-(methyloxy)phenyl]amino}-1,2,4-triazin-6-yl)ethyl]benzamideYield 80.7%

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 2-chlorobenzoic acid (70 mg, 0.45 mmol) to give 2-chloro-N-[1-(3-{[4-(methyloxy)phenyl]amino}-1,2,4-triazin-6-yl)ethyl]benzamide (127 mg) as a yellow solid. MS m/z 384 (M+1).

Sources & evidence

ORD record
ord-7f9c5f1ca29b471c85201cc56f7aa9a0
Source dataset
uspto-grants-2008_12
Patent number
US07462614B2

Reaction notes

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