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Diisopropylethylamine → 3-{[(5-Chloro-thiophene-2-carbonyl)-amino]-methyl}-[1,2,4]oxadiazole-5-carboxylic acid ethyl ester

HRID 2237641
ノート
印刷プレビュー

反応式

HRID 2237641 の反応式
Cl.Cl.[CH2:3]([O:5][C:6]([C:8]1[O:12][N:11]=[C:10]([CH2:13][NH2:14])[N:9]=1)=[O:7])[CH3:4].C(N(C(C)C)C(C)C)C.[Cl:24][C:25]1[S:29][C:28]([C:30](O)=[O:31])=[CH:27][CH:26]=1>CN(C=O)C.CCOC(C)=O.F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1>[CH2:3]([O:5][C:6]([C:8]1[O:12][N:11]=[C:10]([CH2:13][NH:14][C:30]([C:28]2[S:29][C:25]([Cl:24])=[CH:26][CH:27]=2)=[O:31])[N:9]=1)=[O:7])[CH3:4]
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 3

HCID 81531DiisopropylethylamineHCID 950485-Chloro-2-thiophenecarboxylic acidHCID 686910763-Aminomethyl-[1,2,4]oxadiazole-5-carboxylic acid ethyl ester dihydrochloride

生成物 1

HCID 593029563-{[(5-Chloro-thiophene-2-carbonyl)-amino]-methyl}-[1,2,4]oxadiazole-5-carboxylic acid ethyl ester収率 81.6%

試薬・触媒・溶媒 3

HCID 151348
Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphate
触媒
HCID 6228Dimethylformamide溶媒
HCID 8857Ethyl Acetate溶媒

実験手順

To a stirred solution of 3-aminomethyl-[1,2,4]oxadiazole-5-carboxylic acid ethyl ester dihydrochloride (555 mg) at r.t. in DMF (10 ml) under an argon atmosphere were added N-ethyldiisopropylamine (1.82 ml), 5-chloro-2-thiophenecarboxylic acid (565 mg) and BOP (1.54 mg). The mixture was stirred over night, then diluted with EtOAc and washed with H2O. The aqueous phase was back extracted with EtOAc and brine, dried over MgSO4, filtered and concentrated. The crude product was purified by column chromatography (silica gel; gradient: cyclohexane->cyclohexane/EtOAc 1:1) to give 3-{[(5-chloro-thiophene-2-carbonyl)-amino]-methyl}-[1,2,4]oxadiazole-5-carboxylic acid ethyl ester (586 mg) as off-white solid. MS 316.0 ([M+H]+)

後処理

  1. washwashed with H2O
  2. extractionThe aqueous phase was back extracted with EtOAc and brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude product was purified by column chromatography (silica gel; gradient: cyclohexane->cyclohexane/EtOAc 1:1)

出典と根拠

ORDレコード
ord-ec9db8cc7b674cec8394dbecdebe97ee
出典データセット
uspto-grants-2010_05
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07718679B2

反応ノート

読み込み中…

このページの内容参加物実験手順後処理出典と根拠反応ノート