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Water → HCID 58541772、化合物

HRID 600259
ノート
印刷プレビュー

反応式

HRID 600259 の反応式
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[C:10]3[N:14]([C:15]=2[C:16]2[CH:21]=[CH:20][N:19]=[C:18](S(C)(=O)=O)[N:17]=2)[CH:13]=[CH:12][S:11]3)=[CH:4][CH:3]=1.[C:26]([O:30][C:31]([N:33]1[CH2:38][CH2:37][CH:36]([NH2:39])[CH2:35][CH2:34]1)=[O:32])([CH3:29])([CH3:28])[CH3:27].CCN(C(C)C)C(C)C.O>CS(C)=O>[C:26]([O:30][C:31]([N:33]1[CH2:38][CH2:37][CH:36]([NH:39][C:18]2[N:17]=[C:16]([C:15]3[N:14]4[C:10]([S:11][CH:12]=[CH:13]4)=[N:9][C:8]=3[C:5]3[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=3)[CH:21]=[CH:20][N:19]=2)[CH2:35][CH2:34]1)=[O:32])([CH3:29])([CH3:27])[CH3:28]
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 962WaterHCID 81531DiisopropylethylamineHCID 12682914-Amino-1-Boc-piperidineHCID 58541623HCID 58541623、化合物

生成物 1

HCID 58541772HCID 58541772、化合物

試薬・触媒・溶媒 1

HCID 679Dimethyl Sulfoxide溶媒

実験手順

To a solution of 6-(4-fluorophenyl)-5-(2-methanesulfonyl-pyrimidin-4-yl)-imidazo[2,1-b]thiazole (L) (1.05 g, 2.8 mmol) in dimethylsulfoxide (12.0 mL) is added 4-amino-piperidine-1-carboxylic acid tert-butyl ester (1.12 g, 5.6 mmol) followed by Hunig's Base (0.76 mL, 5.6 mmol). The reaction mixture is sealed and set to shake at 100° C. for 12 hours. After cooling to room temperature, water is added (50 mL) and the aqueous phase extracted with ethyl acetate (4×20 mL). The combined organic phase is washed with a saturated, aqueous, sodium chloride solution (3×50 mL) and dried over anhydrous sodium sulfate. The organic phase is filtered and the solvent evaporated in vacuo. The crude product is purified by silica gel column chromatography eluting with ethyl acetate/hexane (3/2). The compound 4-{4-[6-(4-fluorophenyl)-imidazo[2,1-b]thiazol-5-yl]-pyrimidin-2-ylamino}-piperidine-1-carboxylic acid tert-butyl ester (M) (Compound CCXXXIII, Table 2) is obtained as a light yellow solid (1.2 g, 88%); m.p. 209-211° C.;

後処理

  1. customThe reaction mixture is sealed
  2. extractionthe aqueous phase extracted with ethyl acetate (4×20 mL)
  3. washThe combined organic phase is washed with a saturated, aqueous, sodium chloride solution (3×50 mL)
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationThe organic phase is filtered
  6. customthe solvent evaporated in vacuo
  7. customThe crude product is purified by silica gel column chromatography
  8. washeluting with ethyl acetate/hexane (3/2)

出典と根拠

ORDレコード
ord-11ff39cae8564b7ab71073991641f3e3
出典データセット
uspto-grants-2011_03
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07902192B2

反応ノート

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