Triethylamine → (S)-2-(4-(5-(4-isopropyl-2-oxooxazolidin-3-yl)pyrazolo[1,5-a]pyrimidin-3-yl)benzoyl)hydrazinecarbothioamide

HRID 539001ノート

反応式

HRID 539001 の反応式
CCN=C=NCCCN(C)C.[CH:12]([C@H:15]1[CH2:19][O:18][C:17](=[O:20])[N:16]1[C:21]1[CH:26]=[CH:25][N:24]2[N:27]=[CH:28][C:29]([C:30]3[CH:38]=[CH:37][C:33]([C:34](O)=[O:35])=[CH:32][CH:31]=3)=[C:23]2[N:22]=1)([CH3:14])[CH3:13].C1C=CC2N(O)N=NC=2C=1.O.[NH:50]([C:52](=[S:54])[NH2:53])[NH2:51].C(N(CC)CC)C>CN(C=O)C.CCOC(C)=O>[CH:12]([C@H:15]1[CH2:19][O:18][C:17](=[O:20])[N:16]1[C:21]1[CH:26]=[CH:25][N:24]2[N:27]=[CH:28][C:29]([C:30]3[CH:31]=[CH:32][C:33]([C:34]([NH:51][NH:50][C:52](=[S:54])[NH2:53])=[O:35])=[CH:37][CH:38]=3)=[C:23]2[N:22]=1)([CH3:13])[CH3:14]

参加物

8

反応物 5

HCID 8471TriethylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 2723789ThiosemicarbazideHCID 27960291-Hydroxybenzotriazole hydrateHCID 67034480(S)-4-(5-(4-isopropyl-2-oxooxazolidin-3-yl)pyrazolo[1,5-a]pyrimidin-3-yl)benzoic acid

生成物 1

HCID 86667822(S)-2-(4-(5-(4-isopropyl-2-oxooxazolidin-3-yl)pyrazolo[1,5-a]pyrimidin-3-yl)benzoyl)hydrazinecarbothioamide収率 33.8%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒2 回HCID 8857Ethyl Acetate溶媒

実験手順

EDCI (157 mg, 0.819 mmol) was added to a mixture of (S)-4-(5-(4-isopropyl-2-oxooxazolidin-3-yl)pyrazolo[1,5-a]pyrimidin-3-yl)benzoic acid (Example 9, Step 1; 50 mg, 0.136 mmol) and HOBT-H2O (62.7 mg, 0.409 mmol) in DMF (2 mL) at ambient temperature, and the reaction mixture was stirred for 20 minutes at ambient temperature. 1.0 mL of hydrazinecarbothioamide (12.4 mg, 0.136 mmol) in DMF and triethylamine (95 μL, 0.682 mmol) were added. The resulting mixture was stirred for 1 hour at ambient temperature. The reaction mixture was diluted with EtOAc, washed with aqueous NH4Cl, NaHCO3, and brine, dried over MgSO4, and concentrated under reduced pressure. The crude material was purified by silica gel flash column chromatography (0-5% MeOH in dichloromethane) to afford 20.2 mg (21%) of (S)-2-(4-(5-(4-isopropyl-2-oxooxazolidin-3-yl)pyrazolo[1,5-a]pyrimidin-3-yl)benzoyl)hydrazinecarbothioamide. LCMS (APCI−) m/z 438.4 [M−H]+.

後処理

  1. stirringThe resulting mixture was stirred for 1 hour at ambient temperature
  2. washwashed with aqueous NH4Cl, NaHCO3, and brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated under reduced pressure
  5. customThe crude material was purified by silica gel flash column chromatography (0-5% MeOH in dichloromethane)

出典と根拠

ORDレコード
ord-918dba0c01564fd0b80afe279743fcd7
出典データセット
uspto-grants-2014_10
特許番号
US08865726B2

反応ノート

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