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

HRID 2268883
Notes
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Reaction equation

HRID 2268883 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.CCCCCC.C(OCC)(=O)C>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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 947NitrogenHCID 8083MorpholineHCID 186292104-Chloro-1-[(3,5-dichloropyridin-4-yl)methyl]-6-methoxyphthalazineHCID 21226206Ethyl acetate hexane

Product 1

HCID 99092171-(3,5-Dichloro-pyridin-4-ylmethyl)-6-methoxy-4-morpholin-4-yl-phthalazineYield 79%

Reagents, catalysts & solvents 1

HCID 6228
Dimethylformamide
Solvent

Conditions

Temperature
100 °C

Procedure

A solution under stirring and dry N2 of 4-chloro-1-(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

  1. customthe solid partitioned between water and CH2Cl2
  2. washThe organic phase was washed with water
  3. customto give a solid which
  4. customchromatographed (eluent

Sources & evidence

ORD record
ord-3dabbd2e8c80456fbad1280df027890e
Source dataset
uspto-grants-2001_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06329370B1

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes