2-Furancarboxylic acid, hydrazide → N'-(2-amino-7-(2-((2-((2,4-difluorophenyl)(methyl)amino)ethyl)(methyl)amino)ethyl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl)furan-2-carbohydrazide

HRID 2239811Notes

Reaction equation

HRID 2239811 reaction equation
[NH2:1][C:2]1[N:3]=[C:4](Cl)[C:5]2[CH:10]=[CH:9][N:8]([CH2:11][CH2:12][N:13]([CH3:26])[CH2:14][CH2:15][N:16]([C:18]3[CH:23]=[CH:22][C:21]([F:24])=[CH:20][C:19]=3[F:25])[CH3:17])[C:6]=2[N:7]=1.[O:28]1[CH:32]=[CH:31][CH:30]=[C:29]1[C:33]([NH:35][NH2:36])=[O:34]>CN1C(=O)CCC1>[NH2:1][C:2]1[N:3]=[C:4]([NH:36][NH:35][C:33]([C:29]2[O:28][CH:32]=[CH:31][CH:30]=2)=[O:34])[C:5]2[CH:10]=[CH:9][N:8]([CH2:11][CH2:12][N:13]([CH2:14][CH2:15][N:16]([C:18]3[CH:23]=[CH:22][C:21]([F:24])=[CH:20][C:19]=3[F:25])[CH3:17])[CH3:26])[C:6]=2[N:7]=1

Participants

4

Reactant 2

HCID 187312-Furancarboxylic acid, hydrazideHCID 86623468N1-(2-(2-amino-4-chloro-7H-pyrrolo[2,3-d]pyrimidin-7-yl)ethyl)-N2-(2,4-difluorophenyl)-N1,N2-dimethylethane-1,2-diamine

Product 1

HCID 68415842N'-(2-amino-7-(2-((2-((2,4-difluorophenyl)(methyl)amino)ethyl)(methyl)amino)ethyl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl)furan-2-carbohydrazide

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
150 °C

Procedure

The title B compound, N1-(2-(2-amino-4-chloro-7H-pyrrolo[2,3-d]pyrimidin-7-yl)ethyl)-N2-(2,4-difluorophenyl)-N1,N2-dimethylethane-1,2-diamine (196.8 mg, 0.50 mmol) and 2-furoic hydrazide (126.0 mg, 1.0 mmol) are dissolved in 2.0 mL of NMP. The solution is stirred at 150.0° C. for 3 h before it is cooled down to RT. The solvent is removed to afford N′-(2-amino-7-(2-((2-((2,4-difluorophenyl)(methyl)amino)ethyl)(methyl)amino)ethyl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl)furan-2-carbohydrazide. LC/MS showed product as one peak.

Workup

  1. temperatureis cooled down to RT
  2. customThe solvent is removed

Sources & evidence

ORD record
ord-280e44b94a084d89baac4a80999d30fe
Source dataset
uspto-grants-2010_05
Patent number
US07723343B2

Reaction notes

Loading…