Oxane-4-carboxylic acid → N-[1-(3-{[4-(methyloxy)phenyl]amino}-1,2,4-triazin-6-yl)ethyl]tetrahydro-2H-pyran-4-carboxamide

HRID 2374972Notes

Reaction equation

HRID 2374972 reaction equation
Br[C:2]1[CH:6]=CS[C:3]=1[C:7]([NH:9][CH:10]([C:12]1[N:17]=[N:16][C:15]([NH:18][C:19]2[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=2)=[N:14][CH:13]=1)[CH3:11])=[O:8].NC(C1N=NC(NC2C=C[C:40]([O:43]C)=[CH:39]C=2)=NC=1)C.O1CCC(C(O)=O)CC1>>[CH3:26][O:25][C:22]1[CH:21]=[CH:20][C:19]([NH:18][C:15]2[N:16]=[N:17][C:12]([CH:10]([NH:9][C:7]([CH:3]3[CH2:2][CH2:6][O:43][CH2:40][CH2:39]3)=[O:8])[CH3:11])=[CH:13][N:14]=2)=[CH:24][CH:23]=1

Participants

4

Reactant 3

HCID 219302Oxane-4-carboxylic acidHCID 587119833-bromo-N-[1-(3-{[4-(methyloxy)phenyl]amino}1,2,4-triazin-6-yl)ethyl]-2-thiophenecarboxamideHCID 587119996-(1-aminoethyl)-N-[4-(methyloxy)phenyl]-1,2,4-triazin-3-amine2×

Product 1

HCID 58711939N-[1-(3-{[4-(methyloxy)phenyl]amino}-1,2,4-triazin-6-yl)ethyl]tetrahydro-2H-pyran-4-carboxamide

Procedure

In a similar manner as described for Intermediate 49, using 6-(1-aminoethyl)-N-[4-(methyloxy)phenyl]-1,2,4-triazin-3-amine (Intermediate 47) (100 mg, 0.41 mmol), and tetrahydropyran-4-yl-carboxylic acid (58 mg, 0.45 mmol), except the reaction was stirred for 16.5 h and a 10 g SCX cartridge was used, to give N-[1-(3-{[4-(methyloxy)phenyl]amino}-1,2,4-triazin-6-yl)ethyl]tetrahydro-2H-pyran-4-carboxamide (81 mg) as a yellow solid. MS m/z 358 (M+1).

Sources & evidence

ORD record
ord-b13e4191cf7b4b83b8d2b321b669a1f2
Source dataset
uspto-grants-2008_12
Patent number
US07462614B2

Reaction notes

Loading…