3-Methoxyphenyl isocyanate → 6-Arylpyrido[2,3-d]pyrimidine deriv. 68

HRID 3429

Reaction equation

HRID 3429 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[C:9]1[C:29]([NH2:30])=[N:28][C:12]2[N:13]=[C:14]([NH:17][CH2:18][CH2:19][CH2:20][N:21]3[CH2:26][CH2:25][N:24]([CH3:27])[CH2:23][CH2:22]3)[N:15]=[CH:16][C:11]=2[CH:10]=1.[CH3:31][O:32][C:33]1[CH:34]=[C:35]([N:39]=[C:40]=[O:41])[CH:36]=[CH:37][CH:38]=1>CO.CC#N>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[C:9]1[C:29]([NH:30][C:40]([NH:39][C:35]2[CH:36]=[CH:37][CH:38]=[C:33]([O:32][CH3:31])[CH:34]=2)=[O:41])=[N:28][C:12]2[N:13]=[C:14]([NH:17][CH2:18][CH2:19][CH2:20][N:21]3[CH2:26][CH2:25][N:24]([CH3:27])[CH2:23][CH2:22]3)[N:15]=[CH:16][C:11]=2[CH:10]=1

Participants

4

Reactant 2

HCID 878433-Methoxyphenyl isocyanateHCID 53281486-(2,6-dichlorophenyl)-2-N-[3-(4-methylpiperazin-1-yl)propyl]pyrido[2,3-d]pyrimidine-2,7-diamine

Product 1

HCID 53281706-Arylpyrido[2,3-d]pyrimidine deriv. 68Yield 69%

Reagents, catalysts & solvents 1

HCID 21959252Acetonitrile methanolSolvent

Procedure

6-(2,6-Dichlorophenyl)-N2 -[3-(4-methyl-piperazin-1-yl)-propyl]-pyrido[2,3-d]pyrimidine-2,7-diamine (1.0 g) from Example 36 was reacted with 0.334 g of 3-methoxyphenyl isocyanate according to the general procedure of Example 37 to give 0.920 g of 1-{6-(2,6-dichlorophenyl)-2-[3-(4-methyl-piperazin-1-yl)-propylamino]-pyrido[2,3-d]pyrimidin-7-yl}-3-(3-methoxy-phenyl)-urea, ESMS (20/80 MeOH/CH3CN+0.1% AcOH): M+ +H=595; mp 87.5°-92.5° C.

Sources & evidence

ORD record
ord-28a36116f8ad42a28acebdd668b243cb
Source dataset
uspto-grants-1998_03
Patent number
US05733913

Linked notes

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