1,2-Dichloroethane → HCID 66896048、化合物

HRID 1257538ノート

反応式

HRID 1257538 の反応式
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]

参加物

8

反応物 6

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

生成物 1

HCID 66896048HCID 66896048、化合物収率 94%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-f06d4e334b2845758b451b38a9379bea
出典データセット
uspto-grants-2013_06
特許番号
US08461185B2

反応ノート

読み込み中…