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Diisopropylethylamine → [2-(2-Fluoro-6-methoxy-phenyl)-thiazol-4-yl]-(2-methyl-piperidin-1-yl)-methanone

HRID 1990994
ノート
印刷プレビュー

反応式

HRID 1990994 の反応式
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([O:8][CH3:9])[C:3]=1[C:10]1[S:11][CH:12]=[C:13]([C:15]([OH:17])=O)[N:14]=1.[CH2:18]1[C@H:27]2[C@@H:22](CCCC2)[CH2:21][CH2:20][NH:19]1.[CH3:28]CN(C(C)C)C(C)C.C1CN([P+](Br)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F>C(Cl)Cl.O>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([O:8][CH3:9])[C:3]=1[C:10]1[S:11][CH:12]=[C:13]([C:15]([N:19]2[CH2:18][CH2:27][CH2:22][CH2:21][CH:20]2[CH3:28])=[O:17])[N:14]=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 81531DiisopropylethylamineHCID 2733179PyBroPHCID 11083964trans-DecahydroisoquinolineHCID 589248452-(2-Fluoro-6-methoxy-phenyl)-thiazole-4-carboxylic acid

生成物 1

HCID 58924834[2-(2-Fluoro-6-methoxy-phenyl)-thiazol-4-yl]-(2-methyl-piperidin-1-yl)-methanone収率 17.9%

試薬・触媒・溶媒 2

HCID 962
Water
溶媒
HCID 6344Dichloromethane溶媒

実験手順

2-(2-Fluoro-6-methoxy-phenyl)-thiazole-4-carboxylic acid (49.5 mg, 0.2 mmol) from the previous step, trans-decahydro-isoquinoline (TCI America, Portland, Oreg.; 27.8 mg, 0.2 mmol), DIPEA (0.1 mL, 0.57 mmol), and PyBrop (103 mg, 0.22 mmol) were mixed in dry DCM (1 mL) and the mixture was left stirring for overnight at room temperature. To the mixture was added water. The DCM layer was separated and the aqueous layer was extracted with DCM twice. The combined DCM layers were dried under vacuum and purified by C-18 reversed phase HPLC with a gradient of 10-100% Acetonitrile/water to give [2-(2-fluoro-6-methoxy-phenyl)-thiazol-4-yl]-(2-methyl-piperidin-1-yl)-methanone (12 mg, 16%).

後処理

  1. waitthe mixture was left
  2. customThe DCM layer was separated
  3. extractionthe aqueous layer was extracted with DCM twice
  4. dry with materialThe combined DCM layers were dried under vacuum
  5. custompurified by C-18

出典と根拠

ORDレコード
ord-294ddf8108ee4196baab1c4ee00a1295
出典データセット
uspto-grants-2010_01
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07645773B2

反応ノート

読み込み中…

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