Dimethylamine → HCID 9800710, compound

HRID 2268850Notes

Reaction equation

HRID 2268850 reaction equation
[Cl:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([Cl:21])[C:7]=1[CH2:8][C:9]1[C:18]2[C:13](=[CH:14][C:15]([O:19][CH3:20])=[CH:16][CH:17]=2)[CH2:12][NH:11][N:10]=1.N#N.[C:24](N1C=CN=C1)([N:26]1[CH:30]=CN=[CH:27]1)=[O:25].CNC>C1COCC1.C(O)C>[CH3:27][N:26]([CH3:30])[C:24]([N:11]1[N:10]=[C:9]([CH2:8][C:7]2[C:6]([Cl:21])=[CH:5][N:4]=[CH:3][C:2]=2[Cl:1])[C:18]2[C:13](=[CH:14][C:15]([O:19][CH3:20])=[CH:16][CH:17]=2)[CH2:12]1)=[O:25]

Participants

7

Reactant 4

HCID 674DimethylamineHCID 947NitrogenHCID 682631,1'-CarbonyldiimidazoleHCID 9797215Phthalazine, 4-[(3,5-dichloro-4-pyridinyl)methyl]-1,2-dihydro-7-methoxy-

Product 1

HCID 9800710HCID 9800710, compoundYield 36.4%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 4-(3,5-dichloro-pyridin-4-ylmethyl)-7-methoxy-1,2-dihydro-phthalazine (1 g, 3.1 mmoles), prepared as described in example 22, in dry THF (35 ml), under stirring and dry N2 at room temperature, was added with 1,1′-carbonyldiimidazole (0.6 g, 3.72 mmoles), then the mixture was refluxed for 3 hours, cooled, added with 5.6M dimethylamine in ethanol (5 ml) and refluxed again. After 44 hours the mixture was cooled, poured into water/ice and extracted more times with CH2Cl2. The organic phases were washed with 5% NaOH, then with water, anhydrified and concentrated. The residue was flash chromatographed (eluent: hexane/ethyl acetate 1:1), then crystallised from acetonitrile (30 ml) to give 0.44 g of the title compound (yield: 36.4%). m.p.: 160-162GC.

Workup

  1. temperaturethe mixture was refluxed for 3 hours
  2. temperaturecooled
  3. temperaturerefluxed again
  4. temperatureAfter 44 hours the mixture was cooled
  5. extractionextracted more times with CH2Cl2
  6. washThe organic phases were washed with 5% NaOH
  7. concentrationwith water, anhydrified and concentrated
  8. customchromatographed (eluent: hexane/ethyl acetate 1:1)
  9. customcrystallised from acetonitrile (30 ml)

Sources & evidence

ORD record
ord-9fa6547bfb1147fda5010fb6f8cd2857
Source dataset
uspto-grants-2001_12
Patent number
US06329370B1

Reaction notes

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