Water → HCID 86629444, compound

HRID 599288Notes

Reaction equation

HRID 599288 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([NH:8][CH3:9])[C:5]([CH2:10][NH:11][C:12]2[CH:17]=[C:16]([N+:18]([O-])=[O:19])[C:15]([F:21])=[CH:14][C:13]=2[CH3:22])=[CH:4][N:3]=1.CCN(CC)CC.[C:30](Cl)(Cl)=[O:31].[OH2:34]>O1CCOCC1>[Cl:1][C:2]1[N:3]=[CH:4][C:5]2[CH2:10][N:11]([C:12]3[CH:17]=[C:16]([N+:18]([O-:19])=[O:34])[C:15]([F:21])=[CH:14][C:13]=3[CH3:22])[C:30](=[O:31])[N:8]([CH3:9])[C:6]=2[CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6371PhosgeneHCID 8471TriethylamineHCID 86629445HCID 86629445, compound

Product 1

HCID 86629444HCID 86629444, compoundYield 36%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To suspension 2-chloro-5-((4-fluoro-2-methyl-5-nitrophenylamino)methyl)-N-methylpyridin-4-amine (2.04 g, 6.28 mmol) in dioxane (30 mL) was added Et3N (3.50 mL, 25 mmol) and phosgene (20% solution in toluene, 6.90 mL, 12.6 mmol). The reaction mixture was stirred at RT for 2.5 h. Water 30 mL) was added and the mixture was extracted with EtOAc (2×70 mL). The combined organics were washed with brine (15 mL), dried (MgSO4) and concentrated in vacuo. The residue was stirred with EtOAC for 15 min and the precipitate was collected by filtration and dried in vacuo to give 7-chloro-3-(4-fluoro-2-methyl-5-nitrophenyl)-1-methyl-3,4-dihydropyrido[4,3-d]pyrimidin-2(1H)-one (0.785 g, 36% yield). 1H NMR (400 MHz, DMSO-d6): δ 8.31 (s, 1H), 8.11 (s, 1H), 7.61 (s, 1H), 7.15 (s, 1H), 4.94 (s, 1H), 4.61 (s, 1H), 3.26 (s, 3H), 2.22 (s, 3H); MS (ESI) m/z: 351.0 [M+H+].

Workup

  1. extractionthe mixture was extracted with EtOAc (2×70 mL)
  2. washThe combined organics were washed with brine (15 mL)
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated in vacuo
  5. stirringThe residue was stirred with EtOAC for 15 min
  6. filtrationthe precipitate was collected by filtration
  7. customdried in vacuo

Sources & evidence

ORD record
ord-fdc3663befc344f3b6b18cd91310ddee
Source dataset
uspto-grants-2011_03
Patent number
US07897762B2

Reaction notes

Loading…