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-alanyl-L-alaninate

HRID 1968299노트

반응식

HRID 1968299 반응식
[C:1]([O:5][C:6]([NH:8][C@H:9]([C:11]([OH:13])=O)[CH3:10])=[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.FC(F)(F)C(O)=O.[NH2:53][C@H:54]([C:56]([O:58][CH2:59][CH2:60][O:61][C:62]1[CH:67]=[CH:66][C:65]([C:68]2[C:73]([C:74]#[N:75])=[C:72]([N:76]3[CH2:80][CH2:79][CH2:78][CH2:77]3)[N:71]=[C:70]([S:81][CH2:82][C:83]3[N:84]=[C:85]([C:88]4[CH:93]=[CH:92][C:91]([Cl:94])=[CH:90][CH:89]=4)[S:86][CH:87]=3)[C:69]=2[C:95]#[N:96])=[CH:64][CH:63]=1)=[O:57])[CH3:55]>CN(C=O)C.O>[C:1]([O:5][C:6]([NH:8][C@H:9]([C:11]([NH:53][C@H:54]([C:56]([O:58][CH2:59][CH2:60][O:61][C:62]1[CH:67]=[CH:66][C:65]([C:68]2[C:73]([C:74]#[N:75])=[C:72]([N:76]3[CH2:77][CH2:78][CH2:79][CH2:80]3)[N:71]=[C:70]([S:81][CH2:82][C:83]3[N:84]=[C:85]([C:88]4[CH:89]=[CH:90][C:91]([Cl:94])=[CH:92][CH:93]=4)[S:86][CH:87]=3)[C:69]=2[C:95]#[N:96])=[CH:64][CH:63]=1)=[O:57])[CH3:55])=[O:13])[CH3:10])=[O:7])([CH3:2])([CH3:3])[CH3:4]

참가 물질

8

반응물 5

HCID 81531DiisopropylethylamineHCID 85082Tert-butoxycarbonylalanineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 687647022-{4-(2-({(2-(4-chlorophenyl)-1,3-thiazol-4-yl)methyl}sulfanyl)-3,5-dicyano-6-(pyrrolidin-1-yl)pyridin-4-yl)phenoxy}ethyl L-alaninate trifluoroacetate

생성물 1

HCID 594356502-{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-alanyl-L-alaninate

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

실험 절차

26.756 g (141.406 mmol) of N-(tert-butoxycarbonyl)-L-alanine together with 29.572 g (154.261 mmol) of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride, 29.529 g (192.827 mmol) of 1-hydroxy-1H-benzotriazole hydrate and 55.979 ml (321.378 mmol) of N,N-diisopropylethylamine were dissolved in 10 l DMF. 97.60 g (128.551 mmol) of trifluoroacetic acid-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 L-alaninate (1:1) were then added, and the mixture was stirred at room temperature for 3 h. The reaction mixture was stirred into water and extracted with dichloromethane. The organic phase was washed with water, dried over sodium sulfate, filtered and concentrated. The residue was triturated with diethyl ether, and the solid was filtered off with suction and air-dried. This gave 95 g (91% of theory) of the desired target compound.

후처리

  1. extractionextracted with dichloromethane
  2. washThe organic phase was washed with water
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was triturated with diethyl ether
  7. filtrationthe solid was filtered off with suction
  8. customair-dried

출처 및 근거

ORD 기록
ord-5585a0177b574219983de67a47514403
출처 데이터셋
uspto-grants-2013_04
특허 번호
US08420825B2

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