Phenyl isocyanate → 1-[4-Methyl-3-(1-methyl-1H-pyrazolo[3,4-c]pyridin-4-ylethynyl)-phenyl]-3-phenyl-urea

HRID 446926Notes

Reaction equation

HRID 446926 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([NH2:8])=[CH:4][C:3]=1[C:9]#[C:10][C:11]1[CH:16]=[N:15][CH:14]=[C:13]2[N:17]([CH3:20])[N:18]=[CH:19][C:12]=12.[C:21]1([N:27]=[C:28]=[O:29])[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>C(Cl)Cl>[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:28]([NH:27][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[O:29])=[CH:4][C:3]=1[C:9]#[C:10][C:11]1[CH:16]=[N:15][CH:14]=[C:13]2[N:17]([CH3:20])[N:18]=[CH:19][C:12]=12

Participants

4

Reactant 2

HCID 7672Phenyl isocyanateHCID 595364374-Methyl-3-(1-methyl-1H-pyrazolo[3,4-c]pyridin-4-ylethynyl)-phenylamine2×

Product 1

HCID 595364551-[4-Methyl-3-(1-methyl-1H-pyrazolo[3,4-c]pyridin-4-ylethynyl)-phenyl]-3-phenyl-urea

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In analogy to GP 5, 200 mg of 4-methyl-3-(1-methyl-1H-pyrazolo[3,4-c]pyridin-4-ylethynyl)-phenylamine (Intermediate 3.2, 0.4 mmol, 1 eq.) were treated with 47 μL phenyl isocyanate (0.44 mmol, 1.1 eq.) in 4 mL DCM at rt. Aqueous work-up followed by HPLC purification provided the target compound.

Workup

  1. customAqueous work-up followed by HPLC purification
  2. customprovided the target compound

Sources & evidence

ORD record
ord-4cc06a2833994e2c82516a59fdb283b3
Source dataset
uspto-grants-2013_07
Patent number
US08481539B2

Reaction notes

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