Phosphorus oxychloride → HCID 11325199, compound

HRID 2374993Notes

Reaction equation

HRID 2374993 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]([C:21]3[S:22][CH:23]=[CH:24][CH:25]=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]([C:21]2[S:22][CH:23]=[CH:24][CH:25]=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 58712002HCID 58712002, compound2×

Product 1

HCID 11325199HCID 11325199, compoundYield 41.7%

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]-2-thiophenecarboxamide (Intermediate 61) (115 mg, 0.32 mmol), 1,2-dichloroethane (5 mL) and phosphorus oxychloride (0.24 mL, 2.57 mmol), to afford 5-methyl-N-[4-(methyloxy)phenyl]-7-(2-thienyl)imidazo[5,1-f][1,2,4]triazin-2-amine (45 mg) as a yellow solid. MS m/z 338 (M+1).

Sources & evidence

ORD record
ord-c304b33865f94f0888262adc53d7c55d
Source dataset
uspto-grants-2008_12
Patent number
US07462614B2

Reaction notes

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