1,2-Dichloroethane → Tert-butyl 1-(4-(5-(4-isopropyl-5-(pyridin-2-yl)isoxazol-3-yl)-1,2,4-oxadiazol-3-yl)benzyl)azetidine-3-carboxylate

HRID 1951946ノート

反応式

HRID 1951946 の反応式
[CH:1]([C:4]1[C:5]([C:15]([OH:17])=O)=[N:6][O:7][C:8]=1[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][N:10]=1)([CH3:3])[CH3:2].C1C=CC2N(O)N=NC=2C=1.C(N(C(C)C)CC)(C)C.C(Cl)CCl.O[N:42]=[C:43]([C:45]1[CH:62]=[CH:61][C:48]([CH2:49][N:50]2[CH2:53][CH:52]([C:54]([O:56][C:57]([CH3:60])([CH3:59])[CH3:58])=[O:55])[CH2:51]2)=[CH:47][CH:46]=1)[NH2:44].N1C=CC=CC=1C1C(C(F)(F)F)=C(C2ON=C(C3C=CC(CN4CC(C(O)=O)C4)=CC=3)N=2)ON=1>C(#N)C>[CH:1]([C:4]1[C:5]([C:15]2[O:17][N:44]=[C:43]([C:45]3[CH:46]=[CH:47][C:48]([CH2:49][N:50]4[CH2:51][CH:52]([C:54]([O:56][C:57]([CH3:58])([CH3:60])[CH3:59])=[O:55])[CH2:53]4)=[CH:61][CH:62]=3)[N:42]=2)=[N:6][O:7][C:8]=1[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][N:10]=1)([CH3:2])[CH3:3]

参加物

8

反応物 6

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 468359141-(4-(5-(3-(Pyridin-2-yl)-4-(trifluoromethyl)isoxazol-5-yl)-1,2,4-oxadiazol-3-yl)benzyl)azetidine-3-carboxylic acidHCID 580628384-Isopropyl-5-(pyridin-2-yl)isoxazole-3-carboxylic acidHCID 76806751tert-butyl 1-[[4-(N'-hydroxycarbamimidoyl)phenyl]methyl]azetidine-3-carboxylate

生成物 1

HCID 66678392Tert-butyl 1-(4-(5-(4-isopropyl-5-(pyridin-2-yl)isoxazol-3-yl)-1,2,4-oxadiazol-3-yl)benzyl)azetidine-3-carboxylate

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

反応条件

温度
80 °C

実験手順

To a solution of 4-isopropyl-5-(pyridin-2-yl)isoxazole-3-carboxylic acid salt (10.4 mg, approx. 0.045 mmol), HOBt (12.34 mg, 0.081 mmol), and diisopropylethylamine (0.031 mL, 0.179 mmol) in acetonitrile (1 mL) was added EDC (20.2 mg, 0.105 mmol) and tert-butyl 1-(4-(N′-hydroxycarbamimidoyl)benzyl)azetidine-3-carboxylate, Int. 1 (13.68 mg, 0.045 mmol). The reaction mixture was stirred at 80° C. for 5 h. The reaction mixture was concentrated, and the residue was diluted with ethyl acetate (3 mL), washed with a saturated aqueous solution of sodium bicarbonate (1 mL), washed with water (1 mL), washed with brine (1 mL), and dried over anhydrous sodium sulfate. Concentration followed by purification on a preparative TLC plate with ethyl acetate afforded tert-butyl 1-(4-(5-(4-isopropyl-5-(pyridin-2-yl)isoxazol-3-yl)-1,2,4-oxadiazol-3-yl)benzyl)azetidine-3-carboxylate.

後処理

  1. concentrationThe reaction mixture was concentrated
  2. additionthe residue was diluted with ethyl acetate (3 mL)
  3. washwashed with a saturated aqueous solution of sodium bicarbonate (1 mL)
  4. washwashed with water (1 mL)
  5. washwashed with brine (1 mL)
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationConcentration
  8. customfollowed by purification on a preparative TLC plate with ethyl acetate

出典と根拠

ORDレコード
ord-5b34bac31d254acf84621cc204bfc0e8
出典データセット
uspto-grants-2013_03
特許番号
US08404672B2

反応ノート

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