Phosphorus oxychloride → HCID 11155130, compound

HRID 2374903Notes

Reaction equation

HRID 2374903 reaction equation
[C:1]([O:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[C:11]([NH:13][CH:14]([C:16]1[N:21]=[N:20][C:19]([NH:22][C:23]2[CH:28]=[C:27]([O:29][CH3:30])[C:26]([O:31][CH3:32])=[C:25]([O:33][CH3:34])[CH:24]=2)=[N:18][CH:17]=1)[CH3:15])=O)(=[O:3])[CH3:2].P(Cl)(Cl)(Cl)=O>ClCCCl.ClCCl.CO.C([O-])([O-])=O.[Na+].[Na+]>[C:1]([O:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[C:11]1[N:21]2[C:16]([CH:17]=[N:18][C:19]([NH:22][C:23]3[CH:28]=[C:27]([O:29][CH3:30])[C:26]([O:31][CH3:32])=[C:25]([O:33][CH3:34])[CH:24]=3)=[N:20]2)=[C:14]([CH3:15])[N:13]=1)(=[O:3])[CH3:2]

Participants

7

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 587119772-{[(1-{3-[(3,4,5-Trimethoxyphenyl)amino]-1,2,4-triazin-6-yl}ethyl)amino]carbonyl}phenyl acetate2×

Product 1

HCID 11155130HCID 11155130, compoundYield 44.5%

Reagents, catalysts & solvents 4

HCID 111,2-DichloroethaneSolventHCID 887MethanolSolventHCID 6344DichloromethaneSolventHCID 10340Sodium CarbonateSolvent

Procedure

To a solution of 2-{[(1-{3-[(3,4,5-trimethoxyphenyl)amino]-1,2,4-triazin-6-yl}ethyl)amino]carbonyl}phenyl acetate (Intermediate 26) (60 mg, 0.13 mmol) in 1,2-dichloroethane (6 mL) was added phosphorous oxychloride (0.10 mL, 1.1 mmol). The mixture was heated to reflux for 5 hours. After cooling to room temperature the reaction was diluted with dichloromethane (125 mL), methanol (20 mL) and aqueous saturated Na2CO3 (40 mL). The aqueous layer was extracted with dichloromethane, then the combined organic layers were dried over MgSO4, concentrated and chromatographed on silica gel, eluting with 2.5% MeOH/DCM to give 2-{5-methyl-2-[(3,4,5-trimethoxyphenyl)amino]imidazo[5,1-f][1,2,4]triazin-7-yl}phenyl acetate (26 mg) as a yellow oil. MS m/z 449 (M+1).

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 5 hours
  3. extractionThe aqueous layer was extracted with dichloromethane
  4. dry with materialthe combined organic layers were dried over MgSO4
  5. concentrationconcentrated
  6. customchromatographed on silica gel
  7. washeluting with 2.5% MeOH/DCM

Sources & evidence

ORD record
ord-2760e92b4e844266a4dab16ca304d4de
Source dataset
uspto-grants-2008_12
Patent number
US07462614B2

Reaction notes

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