Ammonium Acetate → HCID 24967642, compound

HRID 1092356Notes

Reaction equation

HRID 1092356 reaction equation
[CH:1]1([N:4]2[C:8]3([CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]3)[CH2:7][N:6]([C:15]3[CH:23]=[CH:22][C:18]([C:19]([OH:21])=O)=[CH:17][CH:16]=3)[C:5]2=[O:24])[CH2:3][CH2:2]1.C([O-])(=O)C.[NH4+:29]>C1COCC1.CCOC(C)=O>[CH:1]1([N:4]2[C:8]3([CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]3)[CH2:7][N:6]([C:15]3[CH:16]=[CH:17][C:18]([C:19]([NH2:29])=[O:21])=[CH:22][CH:23]=3)[C:5]2=[O:24])[CH2:3][CH2:2]1

Participants

5

Reactant 2

HCID 517165Ammonium AcetateHCID 57495635HCID 57495635, compound

Product 1

HCID 24967642HCID 24967642, compoundYield 19.1%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 76 mg (2.1 mmol) 4-(1-Cyclopropyl-2-oxo-1,3-diaza-spiro[4.6]undec-3-yl)-benzoic acid ethyl ester in 2 ml THF/Methanol 1.1 was treated with 0.5 ml of 1N LiOH. After stirring for 3 h the reaction mixture was acidified with 1N HCL, taken up in EtOAc and washed with water to give 65.5 mg of pure 4-(1-cyclopropyl-2-oxo-1,3-diaza-spiro[4.6]undec-3-yl)-benzoic acid MS (API): 327.5 (M−H). A solution of 47 mg (1.3 mmol) 4-(1-cyclopropyl-2-oxo-1,3-diaza-spiro[4.6]undec-3-yl)-benzoic acid and 27 mg (0.16 mmol) of 1,1-carbonyl diimidazole in 1 ml of THF was stirred under reflux for 1 h, then 32 mg (0.4 mmol) of Ammonium acetate was added and the stirring under reflux was continued for another 2 h. The reaction mixture was taken up in EtOAc and washed with 1N HCL and water. The crude product was crystallized in Ether/Heptan to give 25 mg of pure 4-(1-Cyclopropyl-2-oxo-1,3-diaza-spiro[4.6]undec-3-yl)-benzamide. MS (ESI): 328.4 (MH+).

Workup

  1. temperatureunder reflux for 1 h
  2. temperaturethe stirring under reflux
  3. washwashed with 1N HCL and water
  4. customThe crude product was crystallized in Ether/Heptan

Sources & evidence

ORD record
ord-e649fc5171e44d9abd5ec2fe4cc925a7
Source dataset
uspto-grants-2012_03
Patent number
US08129423B2

Reaction notes

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