Triethylamine → HCID 178440277, compound

HRID 1860558Notes

Reaction equation

HRID 1860558 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[C:4]([Cl:9])[C:3]=1[N:10]1[C:14]2=[N:15][C:16]([CH2:20][C:21]3[CH:26]=[CH:25][C:24]([NH2:27])=[CH:23][CH:22]=3)=[N:17][C:18](=[O:19])[C:13]2=[C:12]([CH:28]([CH3:30])[CH3:29])[NH:11]1.[C:31](N1CCC[C@H]1C(O)=O)([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32].C([N:48]([CH2:51][CH3:52])[CH2:49][CH3:50])C.C[CH2:54][O:55]C(C)=O>CN(C=O)C>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[C:4]([Cl:9])[C:3]=1[N:10]1[C:14]2=[N:15][C:16]([CH2:20][C:21]3[CH:26]=[CH:25][C:24]([N:27]([C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])[C:54](=[O:55])[C@@H:51]4[CH2:52][CH2:50][CH2:49][NH:48]4)=[CH:23][CH:22]=3)=[N:17][C:18](=[O:19])[C:13]2=[C:12]([CH:28]([CH3:30])[CH3:29])[NH:11]1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 850831,2-Pyrrolidinedicarboxylic acid, 1-(1,1-dimethylethyl) ester, (2S)-HCID 178440271HCID 178440271, compound

Product 1

HCID 178440277HCID 178440277, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of 105 mg (0.22 mmol) of 1-(2,4,6-trichlorophenyl)-3-isopropyl-6-(4-aminobenzyl)pyrazolo[3,4-d]pyrimidin-4-one and 235 mg (1.09 mmol) of Boc-L-proline in 2 mL of DMF was added 0.35 mL (2.5 mmol) of triethylamine followed by 490 mg (1.11 mmol) of Bop. The solution was stirred overnight at ambient temperature then poured into EtOAc. This solution was washed sequentally with 0.5 M HCl then dilute aq. Na2CO3 then brine, dried (MgSO4), and concentrated under reduced pressure. The crude product was recrystallized from EtOAc-hexanes to afford 116 mg (80%) of (S)-1-(2,4,6-trichlorophenyl)-3-isopropyl-6-(4-(N-t-butoxycarbonylprolinamido)benzyl)pyrazolo[3,4-d]pyrimidin-4-one as a white solid, mp 225-226° C., Mass spec.: 657 M−H−).

Workup

  1. washThis solution was washed sequentally with 0.5 M HCl
  2. dry with materialdilute aq. Na2CO3 then brine, dried (MgSO4)
  3. concentrationconcentrated under reduced pressure
  4. customThe crude product was recrystallized from EtOAc-hexanes

Sources & evidence

ORD record
ord-e915be3d2d3d429eb280f03947eabd7e
Source dataset
uspto-grants-2003_03
Patent number
US06531477B1

Reaction notes

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