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Triethylamine → Methyl 2-(3-(4-(3-(2-fluorophenyl)ureido)phenyl)isoxazole-5-carboxamido)acrylate

HRID 75834
ノート
印刷プレビュー

反応式

HRID 75834 の反応式
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][C:9](=[O:32])[NH:10][C:11]1[CH:16]=[CH:15][C:14]([C:17]2[CH:21]=[C:20]([C:22]([NH:24][C@@H:25]([CH2:30]O)[C:26]([O:28][CH3:29])=[O:27])=[O:23])[O:19][N:18]=2)=[CH:13][CH:12]=1.CC(C)C(NC(C1ON=C(C2C=CC(NC(NC3C=CC(C(F)(F)F)=CC=3)=O)=CC=2)C=1)=O)C(OC)=O.S(Cl)(C)(=O)=O.CCN(CC)CC>C(Cl)Cl.O>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][C:9](=[O:32])[NH:10][C:11]1[CH:16]=[CH:15][C:14]([C:17]2[CH:21]=[C:20]([C:22]([NH:24][C:25](=[CH2:30])[C:26]([O:28][CH3:29])=[O:27])=[O:23])[O:19][N:18]=2)=[CH:13][CH:12]=1
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 4

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 67352407Methyl 3-methyl-2-(3-(4-(3-(4-(trifluoromethyl)phenyl)ureido)phenyl)isoxazole-5-carboxamido)butanoateHCID 67352794(S)-Methyl 2-(3-(4-(3-(2-fluorophenyl)ureido)phenyl)isoxazole-5-carboxamido)-3-hydroxypropanoate

生成物 1

HCID 67352199Methyl 2-(3-(4-(3-(2-fluorophenyl)ureido)phenyl)isoxazole-5-carboxamido)acrylate
収率 30%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6344Dichloromethane溶媒

実験手順

(S)-methyl 2-(3-(4-(3-(2-fluorophenyl)ureido)phenyl)isoxazole-5-carboxamido)-3-hydroxypropanoate (compound of Example 275, 500 mg, 1.13 mmol) was taken in DCM and mesyl chloride (0.13 ml, 1.69 mmol) and Et3N (0.24, 1.69 mmol) were added and the reaction mixture was stirred at RT for half an hour. Water was added to quench the reaction and the organic layer was extracted with DCM. Organic layer was dried over Na2SO4 and concentrated under vacuum. Crude compound was purified by precipitation using DCM and petroleum ether to yield 140 mg (30%) of the required compound as white solid. MS: ES (+) m/z 425(M+1); 1HNMR (DMSO-d6, 300 MHz) δ: 10.241 (s, 1H), 8.367 (s, 1H), 8.656 (d, 1H), 8.180 (t, 1H), 7.907 (d, 2H), 7.769 (s, 1H), 7.645 (d, 2H), 7.290 (m, 1H), 7.189 (t, 1H), 7.067 (m, 1H), 6.046 (s, 1H), 5.918 (s, 1H), 3.782 (s, 3H).

後処理

  1. customto quench
  2. customthe reaction
  3. extractionthe organic layer was extracted with DCM
  4. dry with materialOrganic layer was dried over Na2SO4
  5. concentrationconcentrated under vacuum
  6. customCrude compound was purified by precipitation

出典と根拠

ORDレコード
ord-bb98e63c638e4b07a324eafa4df40364
出典データセット
uspto-grants-2014_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08835428B2

反応ノート

読み込み中…

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