Hydrochloric Acid → 5-Benzyloxy-4-methoxy-2-(5-methyl-[1,2,4]oxadiazol-3-yl)-N-phenylbenzamide

HRID 2075954노트

반응식

HRID 2075954 반응식
[CH2:1]([O:8][C:9]1[C:10]([O:24][CH3:25])=[CH:11][C:12]([C:18]2[N:22]=[C:21]([CH3:23])[O:20][N:19]=2)=[C:13]([CH:17]=1)[C:14](O)=[O:15])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O[N:27]1[C:31]2[CH:32]=[CH:33][CH:34]=[CH:35][C:30]=2N=N1.NC1C=CC=CC=1.Cl>C(OCC)(=O)C.C(N(CC)CC)C.CN(C)C=O.C(Cl)Cl>[CH2:1]([O:8][C:9]1[C:10]([O:24][CH3:25])=[CH:11][C:12]([C:18]2[N:22]=[C:21]([CH3:23])[O:20][N:19]=2)=[C:13]([CH:17]=1)[C:14]([NH:27][C:31]1[CH:32]=[CH:33][CH:34]=[CH:35][CH:30]=1)=[O:15])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

참가 물질

9

반응물 4

HCID 313Hydrochloric AcidHCID 6115AnilineHCID 757711-HydroxybenzotriazoleHCID 670964845-Benzyloxy-4-methoxy-2-(5-methyl-[1,2,4]oxadiazol-3-yl)benzoic acid

생성물 1

HCID 595656145-Benzyloxy-4-methoxy-2-(5-methyl-[1,2,4]oxadiazol-3-yl)-N-phenylbenzamide수율 730.2%

시약·촉매·용매 4

HCID 6228Dimethylformamide용매HCID 6344Dichloromethane용매HCID 8471Triethylamine용매HCID 8857Ethyl Acetate용매

실험 절차

To a mixture of 5-benzyloxy-4-methoxy-2-(5-methyl-[1,2,4]oxadiazol-3-yl)benzoic acid (reference example 5-1) (500 mg), benzotriazol-1-yloxytripyrrolidinephosphonium hexafluorophosphate (1.15 g), 1-hydroxybenzotriazole (20 mg), methylene chloride (3 mL) and N,N-dimethylformamide (3 mL) were added aniline (0.2 mL) and triethylamine (0.62 mL). After stirring at room temperature for 4 hours, ethyl acetate and 2 mol/L hydrochloric acid were added to the mixture. The separated organic layer was washed with a 2 mol/L aqueous solution of sodium hydroxide, an aqueous solution of sodium bicarbonate and brine successively, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was triturated with methanol to give the title compound (449 mg).

후처리

  1. washThe separated organic layer was washed with a 2 mol/L aqueous solution of sodium hydroxide
  2. dry with materialan aqueous solution of sodium bicarbonate and brine successively, dried over anhydrous magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was triturated with methanol

출처 및 근거

ORD 기록
ord-786d362821414037ad9a1261e8129a2e
출처 데이터셋
uspto-grants-2011_04
특허 번호
US07923462B2

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