Ammonia → HCID 11751833, compound

HRID 13849Notes

Reaction equation

HRID 13849 reaction equation
C([NH:4][C:5]1[C:14]2[C:9](=[N:10][C:11]([C:22]3[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][C:23]=3[Cl:29])=[C:12]([C:15]3[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][CH:16]=3)[CH:13]=2)[N:8]([CH3:30])[C:7](=[O:31])[C:6]=1[C:32]([O:34]C)=O)(=O)C.[NH3:36]>C1COCC1.CO>[NH2:4][C:5]1[C:14]2[C:9](=[N:10][C:11]([C:22]3[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][C:23]=3[Cl:29])=[C:12]([C:15]3[CH:16]=[CH:17][C:18]([Cl:21])=[CH:19][CH:20]=3)[CH:13]=2)[N:8]([CH3:30])[C:7](=[O:31])[C:6]=1[C:32]([NH2:36])=[O:34]

Participants

5

Reactant 2

HCID 222AmmoniaHCID 11307094Methyl 4-(acetylamino)-6(4-chlorophenyl)-7-(2,4-dichlorophenyl)-1-methyl-2-oxo-1,2-dihydro-1,8-naphthyridine-3-carboxylate

Product 1

HCID 11751833HCID 11751833, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To the product of EXAMPLE 91 (30 mg) in THF (1 mL) was added 3 mL of NH3 in methanol (7 M). The reaction stirred for about 15 hours at room temperature before it was concentrated. The residue was dissolved in CH2Cl2 and washed with water. The solution was dried (Na2SO4) and concentrated. The concentrated residue was purified by preparative TLC on silica gel eluted with 100% EtOAc affording the title compound. HPLC/MS: 473.0 (M+1), 475.0 (M+3); Rt=4.19 min.

Workup

  1. concentrationwas concentrated
  2. dissolutionThe residue was dissolved in CH2Cl2
  3. washwashed with water
  4. dry with materialThe solution was dried (Na2SO4)
  5. concentrationconcentrated
  6. customThe concentrated residue was purified by preparative TLC on silica gel
  7. washeluted with 100% EtOAc affording the title compound

Sources & evidence

ORD record
ord-b528aa65a3fd4022894a118dee400691
Source dataset
uspto-grants-2010_06
Patent number
US07728141B2

Reaction notes

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