Tetrahydrofuran → HCID 18545432, compound

HRID 1267085Notes

Reaction equation

HRID 1267085 reaction equation
C1C[O:4][CH2:3]C1.Cl[C:7]1[N:12]=[C:11]([N:13]2[C:17]([CH3:18])=[C:16](/[CH:19]=[CH:20]/[CH2:21][N:22]3[CH2:27][CH2:26][N:25]([C:28]4[CH:33]=[C:32]([F:34])[CH:31]=[C:30]([F:35])[CH:29]=4)[CH2:24][CH2:23]3)[CH:15]=[N:14]2)[CH:10]=[C:9]([CH3:36])[N:8]=1.CO[C:39]1[CH:46]=[CH:45][C:42]([CH2:43][NH2:44])=[CH:41][CH:40]=1.C(=O)([O-])[O-].[K+].[K+]>C(Cl)(Cl)Cl>[F:35][C:30]1[CH:29]=[C:28]([N:25]2[CH2:26][CH2:27][N:22]([CH2:21]/[CH:20]=[CH:19]/[C:16]3[CH:15]=[N:14][N:13]([C:11]4[CH:10]=[C:9]([CH3:36])[N:8]=[C:7]([NH:44][CH2:43][C:42]5[CH:41]=[CH:40][CH:39]=[CH:46][C:45]=5[O:4][CH3:3])[N:12]=4)[C:17]=3[CH3:18])[CH2:23][CH2:24]2)[CH:33]=[C:32]([F:34])[CH:31]=1

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 11430Potassium CarbonateHCID 754524-MethoxybenzylamineHCID 18545346HCID 18545346, compound

Product 1

HCID 18545432HCID 18545432, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To 15 ml of a THF solution of 155 mg of the compound obtained in Example 35 were added 240 mg of p-methoxybenzylamine and 50 mg (0.362 mmol) of potassium carbonate, followed by refluxing for 60 hours. Chloroform was added to the reaction mixture, and the mixture was washed with a saturated sodium chloride aqueous solution. The combined organic layer was dried over anhydrous sodium sulfate, and the solvent was evaporated. The residue was subjected to silica gel column chromatography using a 99:1 mixture (by volume) of chloroform and methanol as a developing solution. The fraction containing the desired compound was concentrated to give 183 mg of the title compound.

Workup

  1. temperatureby refluxing for 60 hours
  2. washthe mixture was washed with a saturated sodium chloride aqueous solution
  3. dry with materialThe combined organic layer was dried over anhydrous sodium sulfate
  4. customthe solvent was evaporated
  5. additionThe fraction containing the desired compound
  6. concentrationwas concentrated

Sources & evidence

ORD record
ord-1174ca4289e1479794b669403921b595
Source dataset
uspto-grants-2003_04
Patent number
US06552018B1

Reaction notes

Loading…