Triethylamine → HCID 86629437, compound

HRID 599264Notes

Reaction equation

HRID 599264 reaction equation
O=C(Cl)[O:3][C:4](Cl)(Cl)Cl.[F:9][C:10]1[CH:15]=[CH:14][C:13]([NH:16][CH2:17][C:18]2[C:19]([NH:28][CH3:29])=[CH:20][C:21]([N:24]([O:26][CH3:27])[CH3:25])=[N:22][CH:23]=2)=[CH:12][C:11]=1[N+:30]([O-:32])=[O:31].CCN(CC)CC.C([O-])([O-])=O.[Na+].[Na+]>O1CCOCC1.O>[F:9][C:10]1[CH:15]=[CH:14][C:13]([N:16]2[CH2:17][C:18]3[CH:23]=[N:22][C:21]([N:24]([O:26][CH3:27])[CH3:25])=[CH:20][C:19]=3[N:28]([CH3:29])[C:4]2=[O:3])=[CH:12][C:11]=1[N+:30]([O-:32])=[O:31]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 10340Sodium CarbonateHCID 10426DiphosgeneHCID 86629434HCID 86629434, compound

Product 1

HCID 86629437HCID 86629437, compoundYield 65%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent2×

Conditions

Temperature
30 °C

Procedure

To a solution of diphosgene (1.15 mL, 9.5 mmol) in anhydrous dioxane (100 mL) was added a mixture of 5-((4-fluoro-3-nitrophenylamino)methyl)-N2-methoxy-N2,N4-dimethylpyridine-2,4-diamine (3.0 g, 9.0 mmol) and Et3N (2.5 mL, 18.0 mmol) in dioxane (200 mL) at 10° C. After addition, the resulting mixture was stirred at 30° C. for 10 h. H2O was added to quench the above reaction and the mixture was neutralized to pH 7 with saturated Na2CO3 solution. The dioxane was removed under reduced pressure and the remaining aqueous solution was extracted with EtOAc (3×50 mL). The combined organics were washed with brine, dried over MgSO4 and concentrated to give 3-(4-fluoro-3-nitrophenyl)-7-(methoxy(methyl)amino)-1-methyl-3,4-dihydropyrido[4,3-d]pyrimidin-2(1H)-one (2.1 g, 65% yield), which was used in the next step without further purification. 1H NMR (300 MHz, DMSO-d6): δ 8.15 (m, 1 H), 7.97 (s, 1 H), 7.80 (m, 1 H), 7.62 (t, J=9.3 Hz, 1 H), 6.58 (s, 1 H), 4.80 (s, 2 H), 3.72 (s, 3 H), 3.27 (s, 3 H), 3.15 (s, 3 H); MS (ESI) m/z: 362.2 (M+H+).

Workup

  1. additionAfter addition
  2. customto quench
  3. customthe above reaction
  4. customThe dioxane was removed under reduced pressure
  5. extractionthe remaining aqueous solution was extracted with EtOAc (3×50 mL)
  6. washThe combined organics were washed with brine
  7. dry with materialdried over MgSO4
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-f907e24df293481cb60930c2f993f8e2
Source dataset
uspto-grants-2011_03
Patent number
US07897762B2

Reaction notes

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