Water → HCID 9801384, compound

HRID 2268862Notes

Reaction equation

[NH:1]1[CH2:5][CH2:4][CH2:3][C:2]1=[O:6].[H-].[Na+].Cl[C:10]1[C:19]2[C:14](=[CH:15][CH:16]=[C:17]([O:20][CH3:21])[CH:18]=2)[C:13]([CH2:22][C:23]2[C:28]([Cl:29])=[CH:27][N:26]=[CH:25][C:24]=2[Cl:30])=[N:12][N:11]=1.O>CN(C=O)C>[Cl:30][C:24]1[CH:25]=[N:26][CH:27]=[C:28]([Cl:29])[C:23]=1[CH2:22][C:13]1[C:14]2[C:19](=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=2)[CH:10]([N:1]2[CH2:5][CH2:4][CH2:3][C:2]2=[O:6])[NH:11][N:12]=1

Participants

Conditions

Temperature: 40 °C

Procedure

A solution of 2-pyrrolidinone (0.14 ml, 1.83 mmoles) in dry DMF (10 ml) under N2 was added with NaH (0.068 g, 1.7 mmoles; 60% in oil) and the mixture was heated to 40° C. for 1 hour, cooled and added with 4-chloro-1-(3,5-dichloro-pyridin-4-ylmethyl)-6-methoxy-phthalazine (0.5 g, 1.41 mmoles), prepared as described in example 45. The mixture was heated to 80° C. overnight, then poured into water (10 volumes) and extracted three times with ethyl acetate. The organic phase was discoloured with charcoal, anhydrified and concentrated to give a solid which was flash chromatographed (eluent: ethyl acetate/petrolatum 9:1). The resultant solid was triturated in ethyl ether and 0.306 g of the title compound were yielded (yield: 53%). m.p.: 223-225° C.

Workup

temperaturecooled
customprepared
temperatureThe mixture was heated to 80° C. overnight
extractionextracted three times with ethyl acetate
concentrationconcentrated
customto give a solid which
customchromatographed (eluent: ethyl acetate/petrolatum 9:1)
customThe resultant solid was triturated in ethyl ether

Sources & evidence

ORD record: ord-b43a17c0c3954b6d86b8f27c8772eb45
Source dataset: uspto-grants-2001_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06329370B1

Reaction notes

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