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

HRID 2075954ノート

反応式

HRID 2075954 の反応式
[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

参加物

9

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 4

HCID 6228Dimethylformamide溶媒HCID 6344Dichloromethane溶媒HCID 8471Triethylamine溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-786d362821414037ad9a1261e8129a2e
出典データセット
uspto-grants-2011_04
特許番号
US07923462B2

反応ノート

読み込み中…