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Diisopropylethylamine → HCID 53349361, 화합물

HRID 2357096
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HRID 2357096 반응식
[C:1]([O:5][C:6]([N:8]1[C@@:12]([CH3:16])([C:13]([OH:15])=O)[CH2:11][O:10][C:9]1([CH3:18])[CH3:17])=[O:7])([CH3:4])([CH3:3])[CH3:2].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(C(C)C)CC)(C)C.[CH2:52]([O:60][C:61]1[CH:70]=[CH:69][C:64]([C:65]([NH:67][NH2:68])=[O:66])=[CH:63][C:62]=1[C:71]([F:74])([F:73])[F:72])[CH2:53][CH2:54][CH2:55][CH2:56][CH2:57][CH2:58][CH3:59]>C(OCC)(=O)C.C(Cl)Cl.CN(C=O)C>[CH3:17][C:9]1([CH3:18])[N:8]([C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7])[C@:12]([CH3:16])([C:13]([NH:68][NH:67][C:65](=[O:66])[C:64]2[CH:69]=[CH:70][C:61]([O:60][CH2:52][CH2:53][CH2:54][CH2:55][CH2:56][CH2:57][CH2:58][CH3:59])=[C:62]([C:71]([F:72])([F:74])[F:73])[CH:63]=2)=[O:15])[CH2:11][O:10]1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 4

HCID 81531Diisopropylethylamine2회HCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)2회HCID 52987736HCID 52987736, 화합물2회HCID 533493604-(Octyloxy)-3-(trifluoromethyl)benzohydrazide2회

생성물 1

HCID 53349361HCID 53349361, 화합물
수율 92.1%

시약·촉매·용매 2

HCID 8857Ethyl Acetate용매HCID 22350042dichloromethane N,N-dimethylformamide용매2회

실험 절차

(R)-3-(tert-Butoxycarbonyl)-2,2,4-trimethyloxazolidine-4-carboxylic acid (D7) (210 mg, 0.81 mmol), HATU (372 mg, 0.98 mmol), diisopropylethyl amine (DIEA) (0.705 mL, 4.1 mmol), CH2Cl2-DMF and 4-(octyloxy)-3-(trifluoromethyl)benzohydrazide (D6) (270 mg, 0.81 mmol) were mixed together. The reaction was condensed, diluted with ethyl acetate, washed with water and brine, and condensed again. Another batch was made using this method with (D7) (0.1 mmol), HATU (46 mg, 0.12 mmol), DIEA (87 mL, 0.5 mmol), CH2Cl2-DMF and 4-(octyloxy)-3-(trifluoromethyl)benzohydrazide (D6) (>6 mg, 0.1 mmol). The batches were chromatographed and combined to provide the title product (428 mg). MS (ESI): 573.84 (MH+); 1H NMR (400 MHz, CDCl3) δ 9.43 (br, 2H), 8.06 (d, 1H, J=2.0 Hz), 7.94 (dd, 1H, J=8.8 Hz, J=2.0 Hz), 6.96 (d, 1H, J=8.8 Hz), 4.52 (br, 1H), 4.07 (t, 2H, J=6.4 Hz), 3.76 (br, 1H), 1.82 (m, 2H), 1.67 (s, 6H), 1.57 (s, 3H), 1.51 (s, 9H), 1.51-1.43 (m, 4H), 1.38-1.24 (m, 6H), 0.88 (t, 3H, J=7.2 Hz).

후처리

  1. customcondensed
  2. washwashed with water and brine, and condensed again
  3. customThe batches were chromatographed

출처 및 근거

ORD 기록
ord-efe41c043629430c93555eec5ee48c60
출처 데이터셋
uspto-grants-2010_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07759370B2

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