Triethylamine → 5-cyclopropyl-8-methoxy-1-(5-methylisoxazole-3-carbonyl)-2,3,5,6-tetrahydrobenzo[b][1,5]diazocin-4(1H)-one

HRID 1614897Notes

Reaction equation

HRID 1614897 reaction equation
[CH:1]1([N:4]2[C:11](=[O:12])[CH2:10][CH2:9][NH:8][C:7]3[CH:13]=[CH:14][C:15]([O:17][CH3:18])=[CH:16][C:6]=3[CH2:5]2)[CH2:3][CH2:2]1.C(N(CC)CC)C.[CH3:26][C:27]1[O:31][N:30]=[C:29]([C:32](Cl)=[O:33])[CH:28]=1>ClC(Cl)C>[CH:1]1([N:4]2[C:11](=[O:12])[CH2:10][CH2:9][N:8]([C:32]([C:29]3[CH:28]=[C:27]([CH3:26])[O:31][N:30]=3)=[O:33])[C:7]3[CH:13]=[CH:14][C:15]([O:17][CH3:18])=[CH:16][C:6]=3[CH2:5]2)[CH2:2][CH2:3]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 27368945-Methylisoxazole-3-carbonyl chlorideHCID 529398795-cyclopropyl-8-methoxy-2,3,5,6-tetrahydrobenzo[b][1,5]diazocin-4(1H)-one

Product 1

HCID 529398825-cyclopropyl-8-methoxy-1-(5-methylisoxazole-3-carbonyl)-2,3,5,6-tetrahydrobenzo[b][1,5]diazocin-4(1H)-oneYield 74%

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

To a solution of 5-cyclopropyl-8-methoxy-2,3,5,6-tetrahydrobenzo[b][1,5]diazocin-4(1H)-one (50.0 mg, 0.203 mmol) from Example 1 in dichloroethane (2.0 ml) was added triethylamine (0.057 ml, 0.406 mmol) and 5-methylisoxazole-3-carbonyl chloride (32.5 mg, 0.223 mmol). The reaction mixture was stirred at room temperature overnight and then quenched with saturated aqueous sodium bicarbonate, followed by extraction with dichloromethane. The combined organic phases were dried over sodium sulfate, filtered and concentrated. Preparative thin layer chromatography (ethyl acetate/methanol:98/2) of the crude residue gave the desired compound (53 mg, 74%).

Workup

  1. customquenched with saturated aqueous sodium bicarbonate
  2. extractionfollowed by extraction with dichloromethane
  3. dry with materialThe combined organic phases were dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-c7f3c11ad5404a5f9df58fbcba1a309c
Source dataset
uspto-grants-2014_07
Patent number
US08765728B2

Reaction notes

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