4-(Trifluoromethyl)phenyl isocyanate → HCID 5328166, compound

HRID 617945Notes

Reaction equation

HRID 617945 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.[F:31][C:32]([F:43])([F:42])[C:33]1[CH:38]=[CH:37][C:36]([N:39]=[C:40]=[O:41])=[CH:35][CH:34]=1>>[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:36]2[CH:35]=[CH:34][C:33]([C:32]([F:31])([F:42])[F:43])=[CH:38][CH:37]=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

3

Reactant 2

HCID 737684-(Trifluoromethyl)phenyl isocyanateHCID 53281486-(2,6-dichlorophenyl)-2-N-[3-(4-methylpiperazin-1-yl)propyl]pyrido[2,3-d]pyrimidine-2,7-diamine

Product 1

HCID 5328166HCID 5328166, compound

Procedure

6-(2, 6-Dichlorophenyl)-N2 -[3-(4-methyl-piperazin-1-yl)-propyl]-pyrido[2,3-d]pyrimidine-2,7-diamine from Example 36 was reacted with trifluoro-p-tolyl isocyanate according to the general procedure of Example 37. Chromatography, eluting first with ethyl acetate:methyl alcohol:triethylamine (90:10:1) then switching to ethyl acetate:ethanol:triethylamine (9:2:1) gave 0.8650 g of the title compound 1-{6-(2,6-dichlorophenyl)-2-[3-(4-methyl-piperazin-1-yl)-propylamino]-pyrido[2,3-d]pyrimidin-7-yl}-3-(4-trifluoromethyl-phenyl)-urea, ESMS (20/80 MeOH/CH3CN +0.1% AcOH): M+ +H=633; mp 145.5-151° C.

Workup

  1. washChromatography, eluting first with ethyl acetate:methyl alcohol:triethylamine (90:10:1)

Sources & evidence

ORD record
ord-688b72ce3e834c96a92a6cd36b67b215
Source dataset
uspto-grants-1999_09
Patent number
US05952342

Reaction notes

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