M-Phenylenediamine → HCID 57635951, compound

HRID 2109980Notes

Reaction equation

HRID 2109980 reaction equation
[CH2:1]([O:3][C:4](=[O:28])[C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([NH:11][C:12]2[N:17]3[N:18]=[CH:19][C:20]([CH2:21][CH2:22][CH2:23][CH2:24][C:25]#[N:26])=[C:16]3[N:15]=[C:14](Cl)[CH:13]=2)[CH:6]=1)[CH3:2].[C:29]1([NH2:36])[CH:34]=[CH:33][CH:32]=[C:31]([NH2:35])[CH:30]=1>CN1C(=O)CCC1.CCOC(C)=O>[CH2:1]([O:3][C:4](=[O:28])[C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([NH:11][C:12]2[N:17]3[N:18]=[CH:19][C:20]([CH2:21][CH2:22][CH2:23][CH2:24][C:25]#[N:26])=[C:16]3[N:15]=[C:14]([NH:35][C:31]3[CH:32]=[CH:33][CH:34]=[C:29]([NH2:36])[CH:30]=3)[CH:13]=2)[CH:6]=1)[CH3:2]

Participants

5

Reactant 2

HCID 7935M-PhenylenediamineHCID 57635949HCID 57635949, compound

Product 1

HCID 57635951HCID 57635951, compoundYield 123.9%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
160 °C

Procedure

A mixture of compound (14a) (0.63 g. 1.6 mmol) and benzene-1,3-diamine (69 mg, 0.636 mmol) in 2 mL of NMP was heated at 160° C. overnight. The reaction mixture was diluted with EtOAc (50 mL) and washed with saturated aq NaHCO3 and brine and dried over anhydrous Na2 SO4. HPLC purification provided 3-[5-(3-amino-phenylamino)-3-(4-cyano-butyl)-pyrazolo[1,5-a]pyrimidin-7-ylamino]-benzoic acid ethyl ester (15a) (0.37 g. 50%).

Workup

  1. washwashed with saturated aq NaHCO3 and brine
  2. customdried over anhydrous Na2 SO4
  3. customHPLC purification

Sources & evidence

ORD record
ord-4f85c1aa3b5e49308dd7343b255c7f4c
Source dataset
uspto-grants-2009_04
Patent number
US07517882B2

Reaction notes

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