1,2-Dichloroethane → HCID 66896048, 화합물

HRID 1257538노트

반응식

HRID 1257538 반응식
Cl.[Br:2][C:3]1[CH:4]=[C:5]([CH:9]=[C:10]([C:12]2[CH2:16][C@@H:15]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][N:18]=3)[O:14][N:13]=2)[CH:11]=1)[C:6]([OH:8])=O.Cl.[F:24][C:25]1[CH:26]=[CH:27][C:28]([C@H:31]([NH2:33])[CH3:32])=[N:29][CH:30]=1.C(Cl)CCl.C1C=NC2N(O)N=NC=2C=1.C(N(CC)CC)C.C(=O)(O)[O-].[Na+]>CN(C)C=O>[Br:2][C:3]1[CH:4]=[C:5]([CH:9]=[C:10]([C:12]2[CH2:16][C@@H:15]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][N:18]=3)[O:14][N:13]=2)[CH:11]=1)[C:6]([NH:33][C@@H:31]([C:28]1[CH:27]=[CH:26][C:25]([F:24])=[CH:30][N:29]=1)[CH3:32])=[O:8]

참가 물질

8

반응물 6

HCID 111,2-DichloroethaneHCID 8471TriethylamineHCID 181649HOAtHCID 516892Sodium BicarbonateHCID 66690953(1R)-1-(5-fluoropyridin-2-yl)ethan-1-amine hydrochlorideHCID 66895359HCID 66895359, 화합물

생성물 1

HCID 66896048HCID 66896048, 화합물수율 94%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a solution of 3-bromo-5-[(5S)-5-(2-pyridinyl)-4,5-dihydro-3-isoxazolyl]benzoic acid hydrochloride (0.476 g, 1.24 mmol) in N,N-dimethylformamide (6 mL) were added (1R)-1-(5-fluoropyridin-2-yl)ethanamine hydrochloride (0.330 g, 1.55 mmol), EDC (416 mg, 2.17 mmol), HOAT (0.051 g, 0.372 mmol) and triethylamine (0.865 mL, 6.20 mmol). The reaction mixture was stirred at ambient temperature for 18 h. Saturated aqueous sodium bicarbonate was added. The mixture was extracted with dichloromethane (3×). The combined organic extracts were washed with brine, dried over magnesium sulfate, filtered and concentrated. Purification by silica gel chromatography (50% hexanes/ethyl acetate→0% hexanes/ethyl acetate) gave the title compound (547 mg). MS 468.9 (M+1).

후처리

  1. extractionThe mixture was extracted with dichloromethane (3×)
  2. washThe combined organic extracts were washed with brine
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customPurification by silica gel chromatography (50% hexanes/ethyl acetate→0% hexanes/ethyl acetate)

출처 및 근거

ORD 기록
ord-f06d4e334b2845758b451b38a9379bea
출처 데이터셋
uspto-grants-2013_06
특허 번호
US08461185B2

반응 노트

불러오는 중…