Pyrrolidine → HCID 58959511, compound

HRID 915853Notes

Reaction equation

HRID 915853 reaction equation
Cl[C:2]1[C:3]2[C:4](=[C:8]([C:18]3[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][CH:19]=3)[N:9]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=3[Cl:17])[N:10]=2)[N:5]=[CH:6][N:7]=1.[NH:25]1[CH2:29][CH2:28][CH2:27][CH2:26]1.C(OCC)(=O)C.CCCCCC>C(O)C>[Cl:24][C:21]1[CH:20]=[CH:19][C:18]([C:8]2[N:9]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=3[Cl:17])[N:10]=[C:3]3[C:2]([N:25]4[CH2:29][CH2:28][CH2:27][CH2:26]4)=[N:7][CH:6]=[N:5][C:4]=23)=[CH:23][CH:22]=1

Participants

5

Reactant 3

HCID 31268PyrrolidineHCID 21226206Ethyl acetate hexaneHCID 58959477HCID 58959477, compound

Product 1

HCID 58959511HCID 58959511, compoundYield 41.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

To a suspension of 7-chloro-3-(4-chlorophenyl)-2-(2-chlorophenyl)-2H-pyrazolo[4,3-d]pyrimidine I-2A-1c (40 mg, 0.1 mmol) in 5 ml ethanol was added pyrrolidine (711 mg, 10 mmol). The reaction mixture was stirred at room temperature for 1 hour and became homogeneous. After the reaction was complete (as monitored by TLC, ethyl acetate/hexane, 50/50), ethanol was removed under reduced pressure. The residue was redissolved in ethyl acetate, washed with water, dried over magnesium sulfate, and concentrated. The crude product was purified by HPLC to give 3-(4-chlorophenyl)-2-(2-chlorophenyl)-7-pyrrolidin-1-yl-2H-pyrazolo[4,3-d]pyrimidine 2A-1 (17 mg, 38.2%). MS: 410.2 (M+1)+; 1H NMR (400 MHz, CD2Cl2) δ 8.3 (s, 1H), 7.5 (m, 6H), 7.3 (d, J=8.7 Hz, 2H), 4.2 (t, J=6.3 Hz, 2H), 3.8 (t, J=7.1 Hz, 2H), 2.1 (m, 4H).

Workup

  1. customwas removed under reduced pressure
  2. dissolutionThe residue was redissolved in ethyl acetate
  3. washwashed with water
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated
  6. customThe crude product was purified by HPLC

Sources & evidence

ORD record
ord-b17fd0998f57435bb2ac35998cd5fe9d
Source dataset
uspto-grants-2007_09
Patent number
US07268133B2

Reaction notes

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