Phosphorus oxychloride → 5-methyl-N-[4-(methyloxy)phenyl]-7-(tetrahydro-2H-pyran-4-yl)imidazo[5,1-f][1,2,4]triazin-2-amine

HRID 2374973Notes

Reaction equation

HRID 2374973 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([NH:9][C:10]2[N:11]=[N:12][C:13]([CH:16]([NH:18][C:19]([CH:21]3[CH2:26][CH2:25][O:24][CH2:23][CH2:22]3)=O)[CH3:17])=[CH:14][N:15]=2)=[CH:5][CH:4]=1.P(Cl)(Cl)(Cl)=O>ClCCCl>[CH3:17][C:16]1[N:18]=[C:19]([CH:21]2[CH2:26][CH2:25][O:24][CH2:23][CH2:22]2)[N:12]2[C:13]=1[CH:14]=[N:15][C:10]([NH:9][C:6]1[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=1)=[N:11]2

Participants

4

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 58711939N-[1-(3-{[4-(methyloxy)phenyl]amino}-1,2,4-triazin-6-yl)ethyl]tetrahydro-2H-pyran-4-carboxamide2×

Product 1

HCID 114392045-methyl-N-[4-(methyloxy)phenyl]-7-(tetrahydro-2H-pyran-4-yl)imidazo[5,1-f][1,2,4]triazin-2-amineYield 44.8%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

Applying the Cyclization Procedure 1, using N-[1-(3-{[4-(methyloxy)phenyl]amino}-1,2,4-triazin-6-yl)ethyl]tetrahydro-2H-pyran-4-carboxamide (Intermediate 50) (81 mg, 0.23 mmol), 1,2-dichloroethane (4.5 mL) and phosphorus oxychloride (0.169 mL, 1.81 mmol), to afford 5-methyl-N-[4-(methyloxy)phenyl]-7-(tetrahydro-2H-pyran-4-yl)imidazo[5,1-f][1,2,4]triazin-2-amine (35 mg) as a yellow solid. MS m/z 340 (M+1).

Sources & evidence

ORD record
ord-ffc69fba924545c495d95ee7e741a049
Source dataset
uspto-grants-2008_12
Patent number
US07462614B2

Reaction notes

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