Diisopropylethylamine → Cannabinoid receptor-2 agonists

HRID 336184ノート

反応式

HRID 336184 の反応式
Cl.[C:2]([C:6]1[O:10][N:9]=[C:8]([NH:11][C:12]([C@@H:14]2[CH2:19][CH2:18][CH2:17][CH2:16][NH:15]2)=[O:13])[CH:7]=1)([CH3:5])([CH3:4])[CH3:3].[O:20]=[S:21]1(=[O:30])[CH2:26][CH2:25][N:24]([C:27](Cl)=[O:28])[CH2:23][CH2:22]1.C(N(CC)C(C)C)(C)C>C1COCC1>[C:2]([C:6]1[O:10][N:9]=[C:8]([NH:11][C:12]([C@@H:14]2[CH2:19][CH2:18][CH2:17][CH2:16][N:15]2[C:27]([N:24]2[CH2:25][CH2:26][S:21](=[O:30])(=[O:20])[CH2:22][CH2:23]2)=[O:28])=[O:13])[CH:7]=1)([CH3:5])([CH3:3])[CH3:4]

参加物

5

反応物 3

HCID 81531DiisopropylethylamineHCID 216949071,1-Dioxo-1lambda6-thiomorpholine-4-carbonyl chlorideHCID 86660400(S)-Piperidine-2-carboxylic acid (5-tert-butyl-isoxazol-3-yl) amide hydrochloride

生成物 1

HCID 70865101Cannabinoid receptor-2 agonists

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a suspension of (S)-Piperidine-2-carboxylic acid (5-tert-butyl-isoxazol-3-yl) amide hydrochloride (150 mg; 0.521 mmol) in THF (6 mL) is added 1,1-Dioxo-1λ6-thiomorpholine-4-carbonyl chloride (102.97 mg; 0.521 mmol) and N,N-diisopropylethylamine (0.186 mL; 1.07 mmol). The reaction mixture is stirred at room temperature for 4 hours. The reaction mixture is quenched with water and extracted with methylene chloride twice. The combined organics were washed with brine, dried over Na2SO4, filtered and concentrated in vacuo. Purification by flash chromatography on silica gel using methanol/methylene chloride provides the title compound, m/z 413 [M+H+].

後処理

  1. customThe reaction mixture is quenched with water
  2. extractionextracted with methylene chloride twice
  3. washThe combined organics were washed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customPurification by flash chromatography on silica gel

出典と根拠

ORDレコード
ord-3a5694dcd6064dd19eb23cbf73c14f35
出典データセット
uspto-grants-2014_11
特許番号
US08889670B2

反応ノート

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