1-Chloro-4-phenylphthalazine → N1-(7-methoxy-1,5-naphthyridin-4-yl)-N1-methyl-N4-(4-phenylphthalazin-1-yl)benzene-1,4-diamine

HRID 1013685Notes

Reaction equation

HRID 1013685 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([C:7]([N:13]([CH3:21])[C:14]3[CH:19]=[CH:18][C:17]([NH2:20])=[CH:16][CH:15]=3)=[CH:8][CH:9]=[N:10]2)=[N:5][CH:4]=1.Cl[C:23]1[C:32]2[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=2)[C:26]([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)=[N:25][N:24]=1>>[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([C:7]([N:13]([CH3:21])[C:14]3[CH:19]=[CH:18][C:17]([NH:20][C:23]4[C:32]5[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=5)[C:26]([C:33]5[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=5)=[N:25][N:24]=4)=[CH:16][CH:15]=3)=[CH:8][CH:9]=[N:10]2)=[N:5][CH:4]=1

Participants

3

Reactant 2

HCID 2721091-Chloro-4-phenylphthalazineHCID 67317033HCID 67317033, compound

Product 1

HCID 59427356N1-(7-methoxy-1,5-naphthyridin-4-yl)-N1-methyl-N4-(4-phenylphthalazin-1-yl)benzene-1,4-diamine

Conditions

Temperature
100 °C

Procedure

A mixture of N1-(7-methoxy-1,5-naphthyridin-4-yl)-N1-methylbenzene-1,4-diamine (0.061 g, 0.22 mmol) and 1-chloro-4-phenylphthalazine (0.052 g, 0.22 mmol) was heated at 100° C. for 48 h. The solvent was removed in vacuo and the residue was purified by silica gel chromatography using 1-10% MeOH:CH2Cl2 containing 1% NH4OH to afford N1-(7-methoxy-1,5-naphthyridin-4-yl)-N1-methyl-N4-(4-phenylphthalazin-1-yl)benzene-1,4-diamine as a yellow solid.

Workup

  1. customThe solvent was removed in vacuo
  2. customthe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-77ade879f4114986aeede2d6c587d663
Source dataset
uspto-grants-2011_07
Patent number
US07981891B2

Reaction notes

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