Triethylamine → HCID 178440277、化合物

HRID 1860558ノート

反応式

HRID 1860558 の反応式
[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

参加物

6

反応物 4

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

生成物 1

HCID 178440277HCID 178440277、化合物収率 80%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

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−).

後処理

  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

出典と根拠

ORDレコード
ord-e915be3d2d3d429eb280f03947eabd7e
出典データセット
uspto-grants-2003_03
特許番号
US06531477B1

反応ノート

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