Triethylamine → HCID 118598879, compound

HRID 1050362Notes

Reaction equation

HRID 1050362 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([NH:8][C:9]2[N:14]=[CH:13][N:12]=[C:11](NC(C3CC3)=O)[CH:10]=2)[C:5](=O)[N:4]2[C:22]([C:27]3C=[CH:31][CH:30]=[C:29](F)[CH:28]=3)(C)[NH:23][C:24](=[O:25])[C:3]=12.C(N(CC)CC)C.Cl.[CH3:42][O:43][NH2:44]>C(Cl)(Cl)Cl>[Cl:1][C:2]1[CH:7]=[C:6]([NH:8][C:9]2[CH:10]=[CH:11][N:12]=[CH:13][N:14]=2)[C:5](=[N:44][O:43][CH3:42])[N:4]2[C:22]3([CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]3)[NH:23][C:24](=[O:25])[C:3]=12

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 521874O-Methylhydroxylamine hydrochlorideHCID 118598561HCID 118598561, compound

Product 1

HCID 118598879HCID 118598879, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of 8′-chloro-6′-(pyrimidin-4-ylamino)-2′H-spiro[cyclohexane-1,3′-imidazo[1,5-a]pyridine]-1′,5′-dione (1, 1 g, 2.89 mmol) in chloroform (30 mL) is added triethylamine (1.21 mL, 8.67 mmol) and O-methylhydroxylamine hydrochloride (241 mg, 2.89 mmol). The reaction is stirred at reflux overnight. The resulting mixture is cooled to room temperature and washed with water. The organic layer is dried over magnesium sulfate, filtered and concentrated. The crude is purified via flash column chromatography to afford 8′-chloro-5′-(methoxyimino)-6′-(pyrimidin-4-ylamino)-2′H-spiro[cyclohexane-1,3′-imidazo[1,5-a]pyridin]-1′(5′H)-one (Cpd. No. 134).

Workup

  1. temperatureat reflux overnight
  2. washwashed with water
  3. dry with materialThe organic layer is dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude is purified via flash column chromatography

Sources & evidence

ORD record
ord-7159d4e7562e4745a081092b81cc418d
Source dataset
uspto-grants-2016_07
Patent number
US09382248B2

Reaction notes

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