2,6-Lutidine → HCID 58065847, 화합물

HRID 62168노트

반응식

HRID 62168 반응식
[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([CH2:16][C:17](=O)[CH2:18][O:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[C:7]3[C:12]([C:13]=2[CH:14]=1)=[CH:11][C:10]([Br:15])=[CH:9][CH:8]=3.N1C(C)=CC=CC=1C.Cl.[CH2:36]([O:43][NH2:44])[C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1>C1COCC1>[CH2:36]([O:43]/[N:44]=[C:17](\[CH2:18][O:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)/[CH2:16][N:6]1[C:7]2[CH:8]=[CH:9][C:10]([Br:15])=[CH:11][C:12]=2[C:13]2[C:5]1=[CH:4][CH:3]=[C:2]([Br:1])[CH:14]=2)[C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1

참가 물질

5

반응물 3

HCID 79372,6-LutidineHCID 102312Benzyloxyamine hydrochlorideHCID 58065823HCID 58065823, 화합물

생성물 1

HCID 58065847HCID 58065847, 화합물수율 93.4%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of the product of Step 1 (17.7 mg, 0.0374 mmol, 1.0 equiv) in THF (400 μL) were added 2,6-lutidine (4.4 μL, 0.0374 mmol, 1.0 equiv), O-benzylhydroxylamine hydrochloride (14.3 mg, 0.0898 mmol, 2.4 equiv) and 4A molecular sieves (15.8 mg). The mixture was stirred for 12 h until TLC indicated complete consumption of starting material. The reaction mixture was quenched with saturated NaHCO3 and extracted 3 times with dichloromethane. The combined organic extracts were dried with MgSO4 and concentrated to give crude product. It was further purified by silica gel chromatography (5-10% EtOAc/Hex) to afford 20.2 mg white solid as product, yield 93.4%. 1H NMR (CDCl3, 400 MHz) δ=4.68 (s, 2H) 5.00 (s, 2H) 5.14 (s, 2H) 6.72 (d, J=8.2 Hz, 2H) 6.94 (t, J=7.3 Hz, 1H) 7.47-7.16 (m, 11H) 8.06 (s, 2H)

후처리

  1. customconsumption of starting material
  2. customThe reaction mixture was quenched with saturated NaHCO3
  3. extractionextracted 3 times with dichloromethane
  4. dry with materialThe combined organic extracts were dried with MgSO4
  5. concentrationconcentrated
  6. customto give crude product
  7. customIt was further purified by silica gel chromatography (5-10% EtOAc/Hex)

출처 및 근거

ORD 기록
ord-94ae204bb6a6425cba6119601dcd057e
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09446022B2

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