Hydrochloric Acid → HCID 18518674、化合物

HRID 1369081

反応式

HRID 1369081 の反応式
[CH2:1]([N:3]([CH2:33][CH3:34])[CH2:4][CH2:5][N:6]1[C:14]2[C:9](=[C:10]([C:17]([F:20])([F:19])[F:18])[CH:11]=[C:12]([C:15]#[N:16])[CH:13]=2)[C:8]([OH:31])([C:21]2[CH:30]=[CH:29][C:28]3[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=3)[CH:22]=2)[C:7]1=[O:32])[CH3:2].Cl.Cl.N1[CH2:42][CH2:41][O:40][CH2:39][CH2:38]1.[OH:43]N1C2C=CC=CC=2N=N1.CCN=C=NCCCN(C)C.Cl.C(N(CC)CC)C>CN(C=O)C.C([O-])(O)=O.[Na+].C(O)(=O)C>[CH2:33]([N:3]([CH2:1][CH3:2])[CH2:4][CH2:5][N:6]1[C:14]2[C:9](=[C:10]([C:17]([F:18])([F:20])[F:19])[CH:11]=[C:12]([C:15]([N:16]3[CH2:42][CH2:41][O:40][CH2:39][CH2:38]3)=[O:43])[CH:13]=2)[C:8]([OH:31])([C:21]2[CH:30]=[CH:29][C:28]3[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=3)[CH:22]=2)[C:7]1=[O:32])[CH3:34]

参加物

10

反応物 6

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 197884Morpholine, hydrochloride (1:1)HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 10961648HCID 10961648、化合物

生成物 1

HCID 18518674HCID 18518674、化合物収率 19.1%

試薬・触媒・溶媒 3

HCID 176Acetic Acid溶媒HCID 6228Dimethylformamide溶媒HCID 516892Sodium Bicarbonate溶媒

実験手順

A mixture of 1-(2-diethylaminoethyl)-4-trifluoromethyl-6-cyano-3-hydroxy-3-(2-naphthyl)oxindole (30 mg, 0.0642 mmol), conc. HCl (2 mL), and acetic acid (2 mL) was heated at reflux for 5 h. Excess solvents were azeotropically removed in vacuo by using toluene to give crude carboxylic acid. The residue was dissolved in DMF (0.5 mL) and morpholine hydrochloride (5.6 mg, 0.0453 mmol), 1-hydroxybenzotriazole (7.5 mg, 0.0555 mmol), WSC HCl (8.5 mg, 0.0443 mmol), and triethylamine (0.04 mL, 0.287 mmol) were added. The mixture was stirred for 16 h at room temperature and diluted with sat. aqueous NaHCO3. The mixture was extracted with ethyl acetate-toluene and the extracts were washed with sat. aqueous NaHCO3, dried over MgSO4, and concentrated. The residue was purified by silica gel column chromatography with 30:1 to 25:1 chloroform/methanol to give the title compound (4.8 mg, 18%).

後処理

  1. temperaturewas heated
  2. temperatureat reflux for 5 h
  3. customExcess solvents were azeotropically removed in vacuo
  4. customto give crude carboxylic acid
  5. extractionThe mixture was extracted with ethyl acetate-toluene
  6. washthe extracts were washed with sat. aqueous NaHCO3
  7. dry with materialdried over MgSO4
  8. concentrationconcentrated
  9. customThe residue was purified by silica gel column chromatography with 30:1 to 25:1 chloroform/methanol

出典と根拠

ORDレコード
ord-985cb356ac97415281436d62d3126398
出典データセット
uspto-grants-2003_06
特許番号
US06576656B1

関連ノート

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