Tetrahydrofuran → HCID 19608045, compound

HRID 745056Notes

Reaction equation

HRID 745056 reaction equation
C([CH:4]1[CH2:13][C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[N:6]([C:14](=[O:32])[C:15]2[CH:20]=[CH:19][C:18]([NH:21][C:22](=[O:31])[C:23]3[CH:28]=[C:27]([Cl:29])[CH:26]=[C:25]([Cl:30])[CH:24]=3)=[CH:17][CH:16]=2)[CH2:5]1)(O)=O.S(Cl)(Cl)=O.[O:37]1[CH2:41][CH2:40][CH2:39][CH2:38]1>>[CH2:41]([O:37][C:22]([NH:21][CH:4]1[CH2:13][C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[N:6]([C:14](=[O:32])[C:15]2[CH:20]=[CH:19][C:18]([NH:21][C:22](=[O:31])[C:23]3[CH:24]=[C:25]([Cl:30])[CH:26]=[C:27]([Cl:29])[CH:28]=3)=[CH:17][CH:16]=2)[CH2:5]1)=[O:31])[C:40]1[CH:13]=[CH:4][CH:5]=[CH:38][CH:39]=1

Participants

4

Reactant 3

HCID 8028TetrahydrofuranHCID 24386Thionyl ChlorideHCID 19607957HCID 19607957, compound

Product 1

HCID 19608045HCID 19608045, compound

Procedure

To 3-carboxy-1-[4-(3,5-dichlorobenzoylamino)benzoyl]-1,2,3,4-tetrahydroquinoline (3.7 g) are added tetrahydrofuran (50 ml) and thionyl chloride (5 ml). The mixture is reacted at 60° C. for 1 hour. The reaction mixture is concentrated and to the residue is added acetone (20 ml). To the mixture is added dropwise a solution of sodium azide (1.0 g) in water (5 ml) under ice-cooling. The reaction mixture is stirred at the same temperature for 30 minutes and extracted with dichloromethane, dried over magnesium sulfate. The solvent is concentrated and to the resulting residue are added anhydrous toluene (30 ml) and benzyl alcohol (1.7 g). The mixture is refluxed for 1 hour. The reaction mixture is concentrated and the resulting residue is purified by silica gel column chromatography (eluent; dichloromethane→dichloromethane:methanol=50:1) to give 3-benzyloxycarbonylamino-1-[4-(3,5-dichlorobenzoylamino)benzoyl)-1,2,3,4-tetrahydroquinoline (3.7 g) as colorless amorphous.

Workup

  1. customThe mixture is reacted at 60° C. for 1 hour
  2. concentrationThe reaction mixture is concentrated and to the residue
  3. additionis added acetone (20 ml)
  4. additionTo the mixture is added dropwise a solution of sodium azide (1.0 g) in water (5 ml) under ice-
  5. temperaturecooling
  6. extractionextracted with dichloromethane
  7. dry with materialdried over magnesium sulfate
  8. concentrationThe solvent is concentrated and to the resulting residue
  9. additionare added anhydrous toluene (30 ml) and benzyl alcohol (1.7 g)
  10. temperatureThe mixture is refluxed for 1 hour
  11. concentrationThe reaction mixture is concentrated
  12. customthe resulting residue is purified by silica gel column chromatography (eluent; dichloromethane→dichloromethane:methanol=50:1)

Sources & evidence

ORD record
ord-637ffb1c9d7140c4ba0fe05933316184
Source dataset
uspto-grants-1996_09
Patent number
US05559230

Reaction notes

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