Hydrochloric Acid → HCID 21354520、化合物

HRID 396368ノート

反応式

HRID 396368 の反応式
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[C:10]([CH:28]3[CH2:33][CH2:32][N:31](C(OCC)=O)[CH2:30][CH2:29]3)[S:11][C:12]=2[C:13]2[CH:18]=[CH:17][N:16]=[C:15]([NH:19][C@H:20]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[CH3:21])[CH:14]=2)=[CH:4][CH:3]=1.[Si](I)(C)(C)C.Cl.[OH-].[Na+]>C(Cl)(Cl)Cl.C(O)CC>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[C:10]([CH:28]3[CH2:33][CH2:32][NH:31][CH2:30][CH2:29]3)[S:11][C:12]=2[C:13]2[CH:18]=[CH:17][N:16]=[C:15]([NH:19][C@H:20]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[CH3:21])[CH:14]=2)=[CH:4][CH:3]=1

参加物

7

反応物 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 85247Trimethylsilyl iodide2 回HCID 60003258HCID 60003258、化合物

生成物 1

HCID 21354520HCID 21354520、化合物収率 71%

試薬・触媒・溶媒 2

HCID 10311-Propanol溶媒HCID 6212Chloroform溶媒

実験手順

4-(4-Fluorophenyl)-2-(1-ethoxycarbonylpiperidin-4-yl)-5-(2-(1-(S)-phenylethyl)amino-4-pyridinyl)thiazole (2 g 3.7 mmol) is dissolved in CHCl3 (37 ml) and treated with Me3SiI (1.5 ml 11.1 mmol) at 60° C. for 5 h. A second portion of Me3SiI (0.75 ml 5.55 mmol ) was added and stirring continued for another 3 h at 60° C. The reaction mixture was combined with 6M HCl in propanol (15 ml), homogenized by vigorous stirring, poured on 2N NaOH and extracted twice with CH2Cl2. The combined organic phases were dried over Na2SO4, filtered, evaporated to dryness and purified by SiO2 chromatography (tert.butyl methyl ether/MeOH/NH3conc. 80/18/2) to yield the title compound (1.2 g 71%) as a white foam.

後処理

  1. stirringhomogenized by vigorous stirring
  2. extractionextracted twice with CH2Cl2
  3. dry with materialThe combined organic phases were dried over Na2SO4
  4. filtrationfiltered
  5. customevaporated to dryness
  6. custompurified by SiO2 chromatography (tert.butyl methyl ether/MeOH/NH3conc. 80/18/2)

出典と根拠

ORDレコード
ord-487dc290665249688bccd1e36eeeef8a
出典データセット
uspto-grants-2003_08
特許番号
US06608072B1

反応ノート

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