Ammonium Chloride → HCID 118598596, compound

HRID 1050398Notes

Reaction equation

HRID 1050398 reaction equation
N(=[C:3]([C:21]1[CH:26]=[CH:25][N:24]=[CH:23][N:22]=1)[C:4]1[C:9](=[O:10])[N:8]2[C:11]3([CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]3)[NH:12][C:13](=[O:14])[C:7]2=[C:6]([CH3:20])[CH:5]=1)N.CC(C)([O-])C.[K+].[Cl-].[NH4+]>C1(C)C=CC=CC=1.ClCCl>[CH3:20][C:6]1[CH:5]=[C:4]([CH2:3][C:21]2[CH:26]=[CH:25][N:24]=[CH:23][N:22]=2)[C:9](=[O:10])[N:8]2[C:11]3([CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]3)[NH:12][C:13](=[O:14])[C:7]=12

Participants

6

Reactant 3

HCID 25517Ammonium ChlorideHCID 23665647Potassium tert-butoxideHCID 123633478HCID 123633478, compound

Product 1

HCID 118598596HCID 118598596, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 6′-(hydrazono(pyrimidin-4-yl)methyl)-8′-methyl-2′H-spiro[cyclohexane-1,3′-imidazo[1,5-a]pyridine]-1′,5′-dione (4, 100 mg, 0.28 mmol) in toluene (4 mL) is added potassium tert-butoxide (94 mg, 0.84 mmol). The reaction is refluxed overnight. The resulting mixture is cooled to room temperature, diluted with dichloromethane and is hed with 1 M ammonium chloride solution. The organic layer is dried over magnesium sulfate, filtered and concentrated. The crude is purified via HPLC to afford 8′-methyl-6′-(pyrimidin-4-ylmethyl)-2′H-spiro[cyclohexane-1,3′-imidazo[1,5-a]pyridine]-1′,5′-dione (Cpd. No. 212).

Workup

  1. temperatureThe reaction is refluxed overnight
  2. dry with materialThe organic layer is dried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe crude is purified via HPLC

Sources & evidence

ORD record
ord-e60ecbe800e4427a85396e5c3d458c5f
Source dataset
uspto-grants-2016_07
Patent number
US09382248B2

Reaction notes

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