Hydrochloric Acid → HCID 178502157, 화합물

HRID 79902노트

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HRID 79902 반응식
[CH3:1][O:2][C:3](=[O:48])[NH:4][CH:5]([C:9]([N:11]1[CH2:15][CH2:14][CH2:13][CH:12]1[C:16]1[NH:17][CH:18]=[C:19]([C:21]2[CH:30]=[CH:29][C:28]3[C:23](=[CH:24][CH:25]=[C:26]([C:31]4[CH:36]=[CH:35][C:34]([C:37](=[O:47])[CH2:38][NH:39][C:40](OC(C)(C)C)=[O:41])=[CH:33][CH:32]=4)[CH:27]=3)[CH:22]=2)[N:20]=1)=[O:10])[CH:6]([CH3:8])[CH3:7].Cl.CCN(C(C)C)C(C)C.[C:59]([O:63][C:64]([N:66]1[CH2:70][CH:69]([C:71]2[CH:76]=[CH:75][CH:74]=[CH:73][CH:72]=2)[CH2:68][CH:67]1C(O)=O)=[O:65])([CH3:62])([CH3:61])[CH3:60].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>C(Cl)Cl.O1CCOCC1.CN(C=O)C.CCOC(C)=O>[C:59]([O:63][C:64]([N:66]1[CH2:70][CH:69]([C:71]2[CH:76]=[CH:75][CH:74]=[CH:73][CH:72]=2)[CH2:68][CH:67]1[C:40](=[O:41])[NH:39][CH2:38][C:37]([C:34]1[CH:35]=[CH:36][C:31]([C:26]2[CH:25]=[CH:24][C:23]3[C:28](=[CH:29][CH:30]=[C:21]([C:19]4[N:20]=[C:16]([CH:12]5[CH2:13][CH2:14][CH2:15][N:11]5[C:9](=[O:10])[CH:5]([NH:4][C:3]([O:2][CH3:1])=[O:48])[CH:6]([CH3:8])[CH3:7])[NH:17][CH:18]=4)[CH:22]=3)[CH:27]=2)=[CH:32][CH:33]=1)=[O:47])=[O:65])([CH3:61])([CH3:62])[CH3:60]

참가 물질

10

반응물 5

HCID 313Hydrochloric AcidHCID 81531Diisopropylethylamine2회HCID 47125061-(1,1-Dimethylethyl) 4-phenyl-1,2-pyrrolidinedicarboxylateHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 178502158{1-[2-(4-{6-[4-(2-Tert-butoxycarbonylamino-acetyl)-phenyl]-naphthalen-2-yl}-1h-imidazol-2-yl)-pyrrolidine-1-carbonyl]-2-methyl-propyl}-carbamic acid methyl ester

생성물 1

HCID 178502157HCID 178502157, 화합물수율 174.4%

시약·촉매·용매 4

HCID 6228Dimethylformamide용매HCID 6344Dichloromethane용매HCID 8857Ethyl Acetate용매HCID 312751,4-Dioxane용매

실험 절차

{1-[2-(4-{6-[4-(2-tert-Butoxycarbonylamino-acetyl)-phenyl]-naphthalen-2-yl}-1H-imidazol-2-yl)-pyrrolidine-1-carbonyl]-2-methyl-propyl}-carbamic acid methyl ester (61.0 mg, 0.095 mmol) was dissolved in DCM (1 mL) and HCl in dioxane (4M, 1 mL) was added and stirring at room temperature was continued. After 90 minutes, all volatiles were removed in vacuo. The crude material was used in the next step without further purification. The crude material was dissolved in DMF (1.0 mL) and DIEA (23.7 mg, 0.183 mmol) was added. A solution of 4-Phenyl-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester (17.8 mg, 0.061 mmol), HATU (23.3 mg, 0.061 mmol) and DIEA (7.9 mg, 0.061 mmol) in DMF (0.5 mL) was added. The reaction was stirred at room temperature. After 20 minutes, the reaction was diluted with EtOAc and was washed with brine, saturated sodium bicarbonate solution, brine, and was dried over sodium sulfate. Filtration and removal of solvents in vacuo gave the crude material (88 mg), which was used in the next step without further purification.

후처리

  1. customall volatiles were removed in vacuo
  2. customThe crude material was used in the next step without further purification
  3. dissolutionThe crude material was dissolved in DMF (1.0 mL)
  4. stirringThe reaction was stirred at room temperature
  5. waitAfter 20 minutes
  6. washwas washed with brine, saturated sodium bicarbonate solution, brine
  7. dry with materialwas dried over sodium sulfate
  8. filtrationFiltration and removal of solvents in vacuo

출처 및 근거

ORD 기록
ord-6e8b73b10e50474787411121dbcc3b26
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08841278B2

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