Triethylamine → HCID 9895731, compound

HRID 636551Notes

Reaction equation

HRID 636551 reaction equation
[CH:1]([O:4][C:5]([C:7]1[C:12](=[O:13])[N:11]2[C:14]([CH2:24][N:25]([CH3:33])[CH2:26][C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)=[C:15]([C:17]3[CH:22]=[CH:21][C:20]([NH2:23])=[CH:19][CH:18]=3)[N:16]=[C:10]2[N:9]([CH2:34][C:35]2[C:40]([F:41])=[CH:39][CH:38]=[CH:37][C:36]=2[F:42])[CH:8]=1)=[O:6])([CH3:3])[CH3:2].[C:43]([N:50]1C=CN=C1)(N1C=CN=C1)=[O:44].C(N(CC)CC)C.Cl.[CH3:63][O:64]N>ClCCl.O.C(Cl)(Cl)Cl>[CH:1]([O:4][C:5]([C:7]1[C:12](=[O:13])[N:11]2[C:14]([CH2:24][N:25]([CH3:33])[CH2:26][C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)=[C:15]([C:17]3[CH:18]=[CH:19][C:20]([NH:23][C:43]([NH:50][O:64][CH3:63])=[O:44])=[CH:21][CH:22]=3)[N:16]=[C:10]2[N:9]([CH2:34][C:35]2[C:40]([F:41])=[CH:39][CH:38]=[CH:37][C:36]=2[F:42])[CH:8]=1)=[O:6])([CH3:3])[CH3:2]

Participants

8

Reactant 4

HCID 8471Triethylamine2×HCID 682631,1'-CarbonyldiimidazoleHCID 521874O-Methylhydroxylamine hydrochlorideHCID 22086866HCID 22086866, compound

Product 1

HCID 9895731HCID 9895731, compoundYield 73.4%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of the compound obtained in Example 32 (1.39 g, 2.43 mmol) in dichloromethane (30 ml) are added 1,1′-carbonyldi-imidazole (0.79 g, 4.86 mmol) and triethylamine (0.68 ml, 4.86 mmol) with ice-cooling. Then the mixture is stirred at room temperature for 2 days. To this reaction mixture is added O-methylhydroxyamine hydrochloride(1.02 g, 12.2 mmol) and triethylamine (1.71 ml, 12.2 mmol) with ice-cooling. The reaction mixture is stirred at this temperature for 4 hours. To the residual mixture is added a mixture of chloroform (50 ml) and water (50 ml). The aqueous layer is extracted with chloroform (50 ml). The combined organic extract is dried over Na2SO4 and concentrated under reduced pressure to give the yellow residue, which is chromatographed on silica gel to afford white-brown crystalline solid. The solid is recrystallized from 2-propanol-ethyl acetate-isopropyl ether to afford pale yellow crystals (1.15 g, 73%).

Workup

  1. temperaturecooling
  2. temperaturecooling
  3. stirringThe reaction mixture is stirred at this temperature for 4 hours
  4. additionTo the residual mixture is added
  5. extractionThe aqueous layer is extracted with chloroform (50 ml)
  6. extractionThe combined organic extract
  7. dry with materialis dried over Na2SO4
  8. concentrationconcentrated under reduced pressure
  9. customto give the yellow residue, which
  10. customis chromatographed on silica gel
  11. customto afford white-brown crystalline solid
  12. customThe solid is recrystallized from 2-propanol-ethyl acetate-isopropyl ether

Sources & evidence

ORD record
ord-77d68c1f05dd4feda707dc537748cd35
Source dataset
uspto-grants-2001_02
Patent number
US06194419B1

Reaction notes

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