Diisopropylethylamine → HCID 89907007, 화합물

HRID 525745노트

반응식

HRID 525745 반응식
[CH2:1]([O:3][C:4](=[O:26])[C:5]1[CH:10]=[C:9]([C:11](=[O:24])[NH:12][C:13]2[CH:18]=[CH:17][C:16]([O:19][C:20]([F:23])([F:22])[F:21])=[CH:15][CH:14]=2)[CH:8]=[N:7][C:6]=1Cl)[CH3:2].[NH:27]1[CH2:31][CH2:30][C@@H:29]([OH:32])[CH2:28]1.CCN(C(C)C)C(C)C>CC(O)C>[CH2:1]([O:3][C:4](=[O:26])[C:5]1[CH:10]=[C:9]([C:11](=[O:24])[NH:12][C:13]2[CH:18]=[CH:17][C:16]([O:19][C:20]([F:23])([F:22])[F:21])=[CH:15][CH:14]=2)[CH:8]=[N:7][C:6]=1[N:27]1[CH2:31][CH2:30][C@@H:29]([OH:32])[CH2:28]1)[CH3:2]

참가 물질

5

반응물 3

HCID 81531DiisopropylethylamineHCID 2759337(R)-3-PyrrolidinolHCID 89906862HCID 89906862, 화합물

생성물 1

HCID 89907007HCID 89907007, 화합물

시약·촉매·용매 1

HCID 3776Isopropanol용매

반응 조건

온도
22 °C

실험 절차

A mixture of 2-chloro-5-((4-(trifluoromethoxy)phenyl)carbamoyl)nicotinic acid ethyl ester (Stage 72.5, 3.00 g, 7.7 mmol), (R)-3-pyrrolidinol (0.807 g, 9.26 mmol) and DIPEA (2.19 g, 17.0 mmol) in iPrOH (50 mL) was stirred at 22° C. for 60 min. The solvent was evaporated off under reduced pressure and the residue was dissolved in EtOAc, washed with sat. aq. NaHCO3 and brine, dried over anhydrous Na2SO4 and the solvent was evaporated off under reduced pressure to give the title compound as a foam. HPLC (Condition 4) tR=5.63 min, UPLC-MS (Condition 8) tR=1.06 min, m/z=440.1 [M+H]+; 1H-NMR (400 MHz, DMSO-d6) δ ppm 1.32 (t, J=7.04 Hz, 3H), 1.79-2.01 (m, 2H), 3.09 (d, J=11.73 Hz, 1H), 3.41 (d, J=8.21 Hz, 1H), 3.54 (dd, J=11.73, 4.30 Hz, 1H), 3.65 (dd, J=10.17, 3.52 Hz, 1H), 4.25-4.39 (m, 3H), 4.96 (d, J=3.13 Hz, 1H), 7.34 (d, J=8.21 Hz, 2H), 7.78-7.90 (m, 2H), 8.36 (d, J=2.35 Hz, 1H), 8.81 (d, J=2.35 Hz, 1H), 10.28 (s, 1H).

후처리

  1. customThe solvent was evaporated off under reduced pressure
  2. dissolutionthe residue was dissolved in EtOAc
  3. washwashed with sat. aq. NaHCO3 and brine
  4. dry with materialdried over anhydrous Na2SO4
  5. customthe solvent was evaporated off under reduced pressure

출처 및 근거

ORD 기록
ord-cbfe84d6d9a444208444158ba22922c5
출처 데이터셋
uspto-grants-2016_05
특허 번호
US09340537B2

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