Ethylenediamine → HCID 178440419, compound

HRID 19596Notes

Reaction equation

HRID 19596 reaction equation
[CH2:1]([NH:8][C:9]1[C:10]2[NH:18][N:17]=[C:16]([CH:19]([CH3:21])[CH3:20])[C:11]=2[N:12]=[C:13](Cl)[N:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:22][CH2:23][CH2:24][NH2:25]>CN1CCCC1=O>[CH2:1]([NH:8][C:9]1[C:10]2[NH:18][N:17]=[C:16]([CH:19]([CH3:21])[CH3:20])[C:11]=2[N:12]=[C:13]([NH:22][CH2:23][CH2:24][NH2:25])[N:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 3301EthylenediamineHCID 178440418HCID 178440418, compound

Product 1

HCID 178440419HCID 178440419, compoundYield 56%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

The mixture 138 mg of 7-benzylamino-5-chloro-3-isopropylpyrazolo[4,3-d]pyrimidine (XVI), 0.62 mL of 2-aminoethylamine (20 eq.) and 0.6 mL of N-methyl-2-pyrrolidone was heated at 125° C. for 12 hours. The reaction mixture was evaporated to dryness in vacuo and then chromatographed over silica gel. The mixture of chloroform/methanol/NH4OH (91:9:1) was used as a mobile phase. Yield=56%; mp=145-147° C.; MS (ES+): 326.1 (100%, M+H+). 1H-NMR (300 MHz, CD3OD): 1.41 d (6H, J=6.9 Hz), 3.10 t (2H, J=5.8 Hz), 3.35 sept (1H, J=6.9 Hz), 3.73 t (2H, 5.8 Hz), 4.86 s (2H), 7.34 m (5H).

Workup

  1. customThe reaction mixture was evaporated to dryness in vacuo
  2. customchromatographed over silica gel
  3. additionThe mixture of chloroform/methanol/NH4OH (91:9:1)

Sources & evidence

ORD record
ord-c7be59f8afa94c799a1c60714c8af759
Source dataset
uspto-grants-2010_06
Patent number
US07745450B2

Reaction notes

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