1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → Ethyl 3-[5-(5-{3-cyano-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-1H-indazol-1-yl]propanoate

HRID 2189785ノート

反応式

HRID 2189785 の反応式
[C:1]([C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][C:11]=1[O:12][CH:13]([CH3:15])[CH3:14])[C:6]([OH:8])=O)#[N:2].CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1.O[NH:38][C:39](=[NH:56])[C:40]1[CH:41]=[C:42]2[C:46](=[CH:47][CH:48]=1)[N:45]([CH2:49][CH2:50][C:51]([O:53][CH2:54][CH3:55])=[O:52])[N:44]=[CH:43]2>CN(C=O)C>[C:1]([C:3]1[CH:4]=[C:5]([C:6]2[O:8][N:38]=[C:39]([C:40]3[CH:41]=[C:42]4[C:46](=[CH:47][CH:48]=3)[N:45]([CH2:49][CH2:50][C:51]([O:53][CH2:54][CH3:55])=[O:52])[N:44]=[CH:43]4)[N:56]=2)[CH:9]=[CH:10][C:11]=1[O:12][CH:13]([CH3:15])[CH3:14])#[N:2]

参加物

6

反応物 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide2 回HCID 757711-HydroxybenzotriazoleHCID 21956832RP-101124HCID 178471847HCID 178471847、化合物

生成物 1

HCID 59316802Ethyl 3-[5-(5-{3-cyano-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-1H-indazol-1-yl]propanoate収率 64.9%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
80 °C

実験手順

A mixture of 3-cyano-4-[(1-methylethyl)oxy]benzoic acid (can be prepared as described in WO2005/58848) (371 mg, 1.81 mmol), EDAC (547 mg, 2.85 mmol) and HOBt (437 mg, 2.85 mmol) in DMF (5 ml) was left standing at RT for 10 minutes. Added ethyl 3-{5-[(hydroxyamino)(imino)methyl]-1H-indazol-1-yl}propanoate (D52) (500 mg, 1.81 mmol) and left standing overnight at RT. Added EDAC (200 mg, 1.04 mmol) and left standing for 24 hours. The mixture was heated at 80° C. for 2 days, standing at RT each night. The mixture was heated at 80° C. for a further 4 hours. Added EtOAc (50 ml) and washed with water (60 ml), sat. NaHCO3 (60 ml) and water (60 ml). The EtOAc layer was dried (MgSO4) and the solvent evaporated. Triturating with ethanol gave the title compound (523 mg) as a beige solid. MS (ES): C24H23N5O4 requires 445; found (MH+) 446.

後処理

  1. waitwas left
  2. waitstanding overnight at RT
  3. waitstanding for 24 hours
  4. waitstanding at RT each night
  5. temperatureThe mixture was heated at 80° C. for a further 4 hours
  6. washAdded EtOAc (50 ml) and washed with water (60 ml), sat. NaHCO3 (60 ml) and water (60 ml)
  7. dry with materialThe EtOAc layer was dried (MgSO4)
  8. customthe solvent evaporated
  9. customTriturating with ethanol

出典と根拠

ORDレコード
ord-3d17080500b04bb1bd94f2f2fabf2d54
出典データセット
uspto-grants-2012_12
特許番号
US08324254B2

反応ノート

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