Triethylamine → HCID 178502627, compound

HRID 1050360Notes

Reaction equation

HRID 1050360 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:21])[N:4]2[C:22]([C:27]3[CH:32]=[CH:31][CH:30]=C(F)C=3)([CH3:26])[NH:23][C:24](=O)[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](=[O:21])[N:4]2[C:22]3([CH2:26][CH2:30][CH2:31][CH2:32][CH2:27]3)[NH:23][C:24](=[N:44][O:43][CH3:42])[C:3]=12

Participants

5

Reactant 3

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

Product 1

HCID 178502627HCID 178502627, 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) was added triethylamine (1.21 mL, 8.67 mmol) and O-methylhydroxylamine hydrochloride (241 mg, 2.89 mmol). The reaction was stirred at reflux overnight. The resulting mixture was cooled to room temperature and washed with water. The organic layer was dried over magnesium sulfate, filtered and concentrated. The crude was purified via flash column chromatography to afford 8′-chloro-1′-(methoxyimino)-6′-(pyrimidin-4-ylamino)-1′,2′-dihydro-5′H-spiro[cyclohexane-1,3′-imidazo[1,5-a]pyridin]-5′-one (Cpd. No. 132).

Workup

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

Sources & evidence

ORD record
ord-37beb222d535461bbb03cd5f181a3505
Source dataset
uspto-grants-2016_07
Patent number
US09382248B2

Reaction notes

Loading…