Triphosgene → 1-[4-(4-Methyl-piperazin-1-ylmethyl)-3-trifluoromethyl-phenyl]-3-[3-(1-methyl-1H-pyrazolo[3,4-c]pyridin-4-ylethynyl)-phenyl]-urea

HRID 446928Notes

Reaction equation

HRID 446928 reaction equation
[CH3:1][N:2]1[C:6]2=[CH:7][N:8]=[CH:9][C:10]([C:11]#[C:12][C:13]3[CH:14]=[C:15]([NH2:19])[CH:16]=[CH:17][CH:18]=3)=[C:5]2[CH:4]=[N:3]1.[CH3:20][N:21]1[CH2:26][CH2:25][N:24]([CH2:27][C:28]2[CH:33]=[CH:32][C:31]([NH2:34])=[CH:30][C:29]=2[C:35]([F:38])([F:37])[F:36])[CH2:23][CH2:22]1.Cl[C:40](Cl)([O:42]C(=O)OC(Cl)(Cl)Cl)Cl>C(#N)C>[CH3:20][N:21]1[CH2:26][CH2:25][N:24]([CH2:27][C:28]2[CH:33]=[CH:32][C:31]([NH:34][C:40]([NH:19][C:15]3[CH:16]=[CH:17][CH:18]=[C:13]([C:12]#[C:11][C:10]4[CH:9]=[N:8][CH:7]=[C:6]5[N:2]([CH3:1])[N:3]=[CH:4][C:5]=45)[CH:14]=3)=[O:42])=[CH:30][C:29]=2[C:35]([F:38])([F:36])[F:37])[CH2:23][CH2:22]1

Participants

5

Reactant 3

HCID 94429Triphosgene2×HCID 46838908AP-245922×HCID 595364393-(1-Methyl-1H-pyrazolo[3,4-c]pyridin-4-ylethynyl)-phenylamine2×

Product 1

HCID 442047281-[4-(4-Methyl-piperazin-1-ylmethyl)-3-trifluoromethyl-phenyl]-3-[3-(1-methyl-1H-pyrazolo[3,4-c]pyridin-4-ylethynyl)-phenyl]-urea

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

124 mg of 3-(1-methyl-1H-pyrazolo[3,4-c]pyridin-4-ylethynyl)-phenylamine (Intermediate 3.1, 0.5 mmol, 1 eq.) were dissolved in 9 mL acetonitrile and treated with 163 mg of 4-(4-methyl-piperazin-1-ylmethyl)-3-trifluoromethyl-phenylamine (0.6 mmol, 1 eq.) and 59 mg of triphosgene (0.2 mmol). The reaction mixture was stirred at rt for 4 h after which the same amounts of triphosgene and 4-(4-methyl-piperazin-1-ylmethyl)-3-trifluoromethyl-phenylamine were added once more and stirring at rt was continued for 16 h. Extractive work-up followed by HPLC purification provided the pure target compound.

Workup

  1. additionwere added once more
  2. customExtractive work-up followed by HPLC purification
  3. customprovided the pure target compound

Sources & evidence

ORD record
ord-e039a44aeac84d9e9809389d84505754
Source dataset
uspto-grants-2013_07
Patent number
US08481539B2

Reaction notes

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