Triethylamine → HCID 178440277, 화합물

HRID 411579노트

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HRID 411579 반응식
[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

참가 물질

6

반응물 4

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

생성물 1

HCID 178440277HCID 178440277, 화합물수율 80%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

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−).

후처리

  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

출처 및 근거

ORD 기록
ord-d269b0db8f8948c1a5ef469d4a56177c
출처 데이터셋
uspto-grants-2003_05
특허 번호
US06559152B2

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