2-Chloro-4,5-difluorobenzoyl Isocyanate → 1-(2-Chloro-4,5-difluorobenzoyl)-3-(6-methoxy-2,4-dioxo-1,2,3,4-tetrahydro-quinazolin-7-yl)urea

HRID 887908Notes

Reaction equation

HRID 887908 reaction equation
[NH2:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6](=[O:13])[NH:7][C:8](=[O:12])[NH:9]2)=[CH:4][C:3]=1[O:14][CH3:15].[Cl:16][C:17]1[CH:27]=[C:26]([F:28])[C:25]([F:29])=[CH:24][C:18]=1[C:19]([N:21]=[C:22]=[O:23])=[O:20]>C(#N)C.CN1CCCC1=O>[Cl:16][C:17]1[CH:27]=[C:26]([F:28])[C:25]([F:29])=[CH:24][C:18]=1[C:19]([NH:21][C:22]([NH:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6](=[O:13])[NH:7][C:8](=[O:12])[NH:9]2)=[CH:4][C:3]=1[O:14][CH3:15])=[O:23])=[O:20]

Participants

5

Reactant 2

HCID 115575832-Chloro-4,5-difluorobenzoyl IsocyanateHCID 688051297-Amino-6-methoxyquinazoline-2,4(1H,3H)-dione

Product 1

HCID 690985201-(2-Chloro-4,5-difluorobenzoyl)-3-(6-methoxy-2,4-dioxo-1,2,3,4-tetrahydro-quinazolin-7-yl)ureaYield 30%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

100 mg (0.53 mmol) of 7-amino-6-methoxy-1H-quinazoline-2,4-dione were suspended in 20 ml of acetonitrile and 2 ml of N-methyl-2-pyrrolidinone, and 200 mg (0.97 mmol) of 2-chloro-4,5-difluorobenzoyl isocyanate (example 1a) were added. The reaction mixture was heated to boiling and then quenched with methanol and concentrated in vacuo. The residue was stirred with acetonitrile, and the resulting precipitate was filtered off. 64 mg (30%) of the desired product were obtained.

Workup

  1. temperatureThe reaction mixture was heated
  2. customquenched with methanol
  3. concentrationconcentrated in vacuo
  4. filtrationthe resulting precipitate was filtered off

Sources & evidence

ORD record
ord-9bc5c7779db4419bb87886b92011092f
Source dataset
uspto-grants-2012_08
Patent number
US08247452B2

Reaction notes

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