1-(Isocyanatomethyl)-2-methylbenzene → HCID 86628143, compound

HRID 1685221Notes

Reaction equation

HRID 1685221 reaction equation
[CH3:1][C:2]1[CH:11]=[CH:10][CH:9]=[CH:8][C:3]=1[CH2:4][N:5]=[C:6]=[O:7].[Cl:12][C:13]1[N:18]=[C:17]2[NH:19][N:20]=[C:21]([OH:22])[C:16]2=[C:15]([CH3:23])[CH:14]=1>C1COCC1.CN(C=O)C>[CH3:1][C:2]1[CH:11]=[CH:10][CH:9]=[CH:8][C:3]=1[CH2:4][NH:5][C:6]([N:20]1[C:21](=[O:22])[C:16]2[C:17](=[N:18][C:13]([Cl:12])=[CH:14][C:15]=2[CH3:23])[NH:19]1)=[O:7]

Participants

5

Reactant 2

HCID 27333861-(Isocyanatomethyl)-2-methylbenzeneHCID 178426134HCID 178426134, compound

Product 1

HCID 86628143HCID 86628143, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

136 μl (0.98 mmol) of 2-methylbenzyl isocyanate were added to 150 mg (0.82 mmol) of 6-chloro-4-methyl-1H-pyrazolo[3,4-b]pyridin-3-ol in 10 ml of THF and 2 ml of DMF at room temperature. The reaction mixture was stirred at room temperature for 2 h and left to stand overnight. Concentration was followed by purification by preparative HPLC (PR18, acetonitrile/water 0.1% TFA). Yield: 139 mg (51%), M+H+: 331.18.

Workup

  1. waitleft
  2. waitto stand overnight
  3. concentrationConcentration
  4. customwas followed by purification by preparative HPLC (PR18, acetonitrile/water 0.1% TFA)

Sources & evidence

ORD record
ord-433571cdd99343daaf424781ce77eef4
Source dataset
uspto-grants-2012_04
Patent number
US08148395B2

Reaction notes

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