Nitrogen → 1-(3,5-Dichloro-pyridin-4-ylmethyl)-6-methoxy-4-morpholin-4-yl-phthalazine

HRID 2297453Notes

Reaction equation

N#N.Cl[C:4]1[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([O:14][CH3:15])[CH:12]=2)[C:7]([CH2:16][C:17]2[C:22]([Cl:23])=[CH:21][N:20]=[CH:19][C:18]=2[Cl:24])=[N:6][N:5]=1.[NH:25]1[CH2:30][CH2:29][O:28][CH2:27][CH2:26]1>CN(C=O)C>[Cl:24][C:18]1[CH:19]=[N:20][CH:21]=[C:22]([Cl:23])[C:17]=1[CH2:16][C:7]1[C:8]2[C:13](=[CH:12][C:11]([O:14][CH3:15])=[CH:10][CH:9]=2)[C:4]([N:25]2[CH2:30][CH2:29][O:28][CH2:27][CH2:26]2)=[N:5][N:6]=1

Participants

Conditions

Temperature: 100 °C

Procedure

A solution under stirring and dry N2 of 4-chloro-(3,5-dichloro-pyridin-4-ylmethyl)-6-methoxy-phthalazine (1 g, 2.82 mmoles), prepared as described in example 45, in DMF (25 ml), at room temperature, was added with morpholine (0.73 g, 8.46 mmoles) and the temperature was raised to 100° C. After 14 hours the whole was brought to dryness and the solid partitioned between water and CH2Cl2. The organic phase was washed with water, anhydrified and brought to dryness to give a solid which was flash chromatographed (eluent hexane/ethyl acetate 6:4, then in gradient up to 3:7) to give 0.9 g of the title compound (yield: 79%). m.p.: 179-180° C.

Workup

customthe solid partitioned between water and CH2Cl2
washThe organic phase was washed with water
customto give a solid which
customchromatographed (eluent hexane/ethyl acetate 6:4

Sources & evidence

ORD record: ord-b84e304f358a4beb9db168da17471267
Source dataset: uspto-grants-2002_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06492360B1

Reaction notes

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