Diisopropylethylamine → 2-{4-(2-({(2-(4-Chlorophenyl)-1,3-thiazol-4-yl)methyl}sulfanyl)-3,5-dicyano-6-(pyrrolidin-1-yl)pyridin-4-yl)phenoxy}ethyl N-(tert-butoxycarbonyl)-L-leucinate

HRID 1621319노트

반응식

HRID 1621319 반응식
[C:1]([O:5][C:6]([NH:8][C@H:9]([C:14]([OH:16])=[O:15])[CH2:10][CH:11]([CH3:13])[CH3:12])=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl.CN(C)CCCN=C=NCC.O.ON1C2C=CC=CC=2N=N1.C(N(CC)C(C)C)(C)C.[Cl:49][C:50]1[CH:55]=[CH:54][C:53]([C:56]2[S:57][CH:58]=[C:59]([CH2:61][S:62][C:63]3[C:68]([C:69]#[N:70])=[C:67]([C:71]4[CH:76]=[CH:75][C:74]([O:77][CH2:78][CH2:79]O)=[CH:73][CH:72]=4)[C:66]([C:81]#[N:82])=[C:65]([N:83]4[CH2:87][CH2:86][CH2:85][CH2:84]4)[N:64]=3)[N:60]=2)=[CH:52][CH:51]=1>CN(C=O)C.O>[C:1]([O:5][C:6]([NH:8][C@H:9]([C:14]([O:16][CH2:79][CH2:78][O:77][C:74]1[CH:73]=[CH:72][C:71]([C:67]2[C:66]([C:81]#[N:82])=[C:65]([N:83]3[CH2:84][CH2:85][CH2:86][CH2:87]3)[N:64]=[C:63]([S:62][CH2:61][C:59]3[N:60]=[C:56]([C:53]4[CH:52]=[CH:51][C:50]([Cl:49])=[CH:55][CH:54]=4)[S:57][CH:58]=3)[C:68]=2[C:69]#[N:70])=[CH:76][CH:75]=1)=[O:15])[CH2:10][CH:11]([CH3:12])[CH3:13])=[O:7])([CH3:3])([CH3:2])[CH3:4]

참가 물질

8

반응물 5

HCID 81531DiisopropylethylamineHCID 83170L-Leucine, N-((1,1-dimethylethoxy)carbonyl)-HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 46847262Neladenoson

생성물 1

HCID 687646672-{4-(2-({(2-(4-Chlorophenyl)-1,3-thiazol-4-yl)methyl}sulfanyl)-3,5-dicyano-6-(pyrrolidin-1-yl)pyridin-4-yl)phenoxy}ethyl N-(tert-butoxycarbonyl)-L-leucinate

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

실험 절차

0.89 g (3.82 mmol) of N-(tert-butoxycarbonyl)-L-leucine were initially charged in 10 ml of DMF, and 0.81 g (4.18 mmol) of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride, 0.80 g (5.23 mmol) of 1-hydroxy-1H-benzotriazole hydrate and 1.13 g (8.71 mmol) of N,N-diisopropylethylamine were added. The mixture was stirred until a clear solution had been obtained. 1.00 g (1.74 mmol) of 2-({(2-(4-chlorophenyl)-1,3-thiazol-4-yl)methyl}sulfanyl)-4-(4-(2-hydroxyethoxy)phenyl)-6-(pyrrolidin-1-yl)pyridine-3,5-dicarbonitrile was then added, and the mixture was stirred at room temperature for 18 h. The mixture was added to 300 ml of water. The residue formed was filtered off with suction and washed with 50 ml of water. The crude product was dissolved in 50 ml of dichloromethane. The aqueous phase was separated off and the organic phase was dried over sodium sulfate. Removal of the solvent under reduced pressure gave 1.37 g (100% of theory) of the desired target compound.

후처리

  1. customhad been obtained
  2. stirringthe mixture was stirred at room temperature for 18 h
  3. customThe residue formed
  4. filtrationwas filtered off with suction
  5. washwashed with 50 ml of water
  6. dissolutionThe crude product was dissolved in 50 ml of dichloromethane
  7. customThe aqueous phase was separated off
  8. dry with materialthe organic phase was dried over sodium sulfate
  9. customRemoval of the solvent under reduced pressure
  10. customgave 1.37 g (100% of theory) of the desired target compound

출처 및 근거

ORD 기록
ord-9141a1ce32ad4c0c82ea297a09e57f7b
출처 데이터셋
uspto-grants-2014_07
특허 번호
US08772498B2

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