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Diisopropylethylamine → N-[4-methyl-5-(5-{[(1-methylpiperidin-4-yl)amino]sulfonyl}-2-thienyl)-1,3-thiazol-2-yl]acetamide

HRID 1360858
ノート
印刷プレビュー

反応式

HRID 1360858 の反応式
[C:1]([NH:4][C:5]1[S:6][C:7]([C:11]2[S:15][C:14]([S:16](Cl)(=[O:18])=[O:17])=[CH:13][CH:12]=2)=[C:8]([CH3:10])[N:9]=1)(=[O:3])[CH3:2].[NH2:20][CH:21]1[CH2:26][CH2:25][N:24]([CH3:27])[CH2:23][CH2:22]1.CCN(C(C)C)C(C)C>C(Cl)Cl.CN(C=O)C>[CH3:10][C:8]1[N:9]=[C:5]([NH:4][C:1](=[O:3])[CH3:2])[S:6][C:7]=1[C:11]1[S:15][C:14]([S:16]([NH:20][CH:21]2[CH2:26][CH2:25][N:24]([CH3:27])[CH2:23][CH2:22]2)(=[O:18])=[O:17])=[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

5

反応物 3

HCID 81531DiisopropylethylamineHCID 27375314-Amino-1-methylpiperidineHCID 866225625-[2-(Acetylamino)-4-methyl-1,3-thiazol-5-yl]thiophene-2-sulfonyl chloride

生成物 1

HCID 11998304N-[4-methyl-5-(5-{[(1-methylpiperidin-4-yl)amino]sulfonyl}-2-thienyl)-1,3-thiazol-2-yl]acetamide

試薬・触媒・溶媒 1

HCID 22350042dichloromethane N,N-dimethylformamide
溶媒

実験手順

5-[2-(acetylamino)-4-methyl-1,3-thiazol-5-yl]thiophene-2-sulfonyl chloride, prepared as in Step 1 of Example 9 (110 mg; 0.33 mmol; 1 eq.), is dissolved in a mixture of DCM/DMF(1/1, 10 ml). 4-Amino-1-methylpiperidine (188 mg; 1.65 mmol; 5 eq.) and DIEA (0.17 ml; 0.98 mmol; 3 eq.) are added. After 3 hours, the solvents are evaporated. The crude product is dissolved in DCM and washed with NH4Cl saturated solution, water and dried over MgSO4. After evaporation of the solvents, crude material is dissolved in DCM (3 ml) and title compound precipitated with Et2O affording after filtration, compound (4) as a white powder (120 mg; 90%). 1H NMR (DMSO-d6) δ 1.25 (m, 2H), 1.55 (m, 2H), 1.80 (m, 2H), 2.05 (m, 2H), 2.25 (s, 6H), 2.40 (s, 3H), 3.05 (m, 1H), 6.95 (d, J=3 Hz, 1H), 7.52 (d, J=3 Hz, 1H), 12.23 (m, 1H). M− (ESI): 413.30; M+ (ESI): 415.30. HPLC, Rt: 2.08 min (purity: 99.33%).

後処理

  1. customthe solvents are evaporated
  2. dissolutionThe crude product is dissolved in DCM
  3. washwashed with NH4Cl saturated solution, water
  4. dry with materialdried over MgSO4
  5. customAfter evaporation of the solvents, crude material
  6. dissolutionis dissolved in DCM (3 ml)
  7. customtitle compound precipitated with Et2O affording
  8. filtrationafter filtration, compound (4) as a white powder (120 mg; 90%)

出典と根拠

ORDレコード
ord-0e971dc56ab349298dee0ba2bb3e7075
出典データセット
uspto-grants-2011_02
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07879888B2

反応ノート

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