Triethylamine → HCID 59346938、化合物

HRID 20577ノート

反応式

HRID 20577 の反応式
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH:15]=[C:16]([O:18][C@H:19]([CH3:23])[CH2:20][O:21][CH3:22])[CH:17]=1)[C:12]([OH:14])=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(Cl)(=O)C(Cl)=O.[CH3:30][N:31]1[CH:35]=[CH:34][C:33]([NH2:36])=[N:32]1.C(N(CC)CC)C>CN(C=O)C.C(Cl)Cl>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH:15]=[C:16]([O:18][C@H:19]([CH3:23])[CH2:20][O:21][CH3:22])[CH:17]=1)[C:12]([NH:36][C:33]1[CH:34]=[CH:35][N:31]([CH3:30])[N:32]=1)=[O:14])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

参加物

7

反応物 4

HCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 1372541-Methyl-3-aminopyrazoleHCID 593469053-(benzyloxy)-5-[(1R)-2-methoxy-1-methylethoxy]benzoic acid

生成物 1

HCID 59346938HCID 59346938、化合物

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide触媒HCID 6344Dichloromethane溶媒2 回

実験手順

DMF (2 drops) was added to a solution of 3-(benzyloxy)-5-[(1R)-2-methoxy-1-methylethoxy]benzoic acid (3.79 g, 0.012 mol) and oxalyl chloride (1.25 mL, 0.015 mol) in DCM (60 mL) and stirred for 3 hours, following which the organics were removed in vacuo. The crude material was dissolved in DCM (30 mL) and slowly added, at 0° C., to a stirred suspension of 1-methyl-1H-pyrazol-3-amine (1.22 g, 0.013 mol) and triethylamine (3.5 mL, 0.025 mol) in DCM (30 mL). The mixture was stirred at ambient temperature for 24 hours and the organics evaporated in vacuo. The residue was dissolved in ethyl acetate (100 mL), washed with 1M aqueous hydrochloric acid (50 mL) and brine (50 mL), dried (MgSO4), filtered and evaporated in vacuo to give the crude product which was chromatographed on silica, eluting with a 50% ethyl acetate in isohexane, to give the desired compound. (4.23 g).

後処理

  1. customorganics were removed in vacuo
  2. dissolutionThe crude material was dissolved in DCM (30 mL)
  3. stirringThe mixture was stirred at ambient temperature for 24 hours
  4. customthe organics evaporated in vacuo
  5. dissolutionThe residue was dissolved in ethyl acetate (100 mL)
  6. washwashed with 1M aqueous hydrochloric acid (50 mL) and brine (50 mL)
  7. dry with materialdried (MgSO4)
  8. filtrationfiltered
  9. customevaporated in vacuo
  10. customto give the crude product which
  11. customwas chromatographed on silica
  12. washeluting with a 50% ethyl acetate in isohexane

出典と根拠

ORDレコード
ord-c62a4155cf324b8d838b8d7b448f4108
出典データセット
uspto-grants-2010_06
特許番号
US07745475B2

反応ノート

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