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

HRID 446925Notes

Reaction equation

HRID 446925 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.[C:20]1([N:26]=[C:27]=[O:28])[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>C(Cl)Cl>[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]([NH:19][C:27]([NH:26][C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=4)=[O:28])[CH:16]=[CH:17][CH:18]=3)=[C:5]2[CH:4]=[N:3]1

Participants

4

Reactant 2

HCID 7672Phenyl isocyanateHCID 595364393-(1-Methyl-1H-pyrazolo[3,4-c]pyridin-4-ylethynyl)-phenylamine2×

Product 1

HCID 595364481-[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, 100 mg of 3-(1-methyl-1H-pyrazolo[3,4-c]pyridin-4-ylethynyl)-phenylamine (Intermediate 3.1, 0.26 mmol, 1 eq.) were treated with 31 μL phenyl isocyanate (0.29 mmol, 1.1 eq.) in 2.6 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-f4cd5de3d3714402935930e21b829a77
Source dataset
uspto-grants-2013_07
Patent number
US08481539B2

Reaction notes

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