Acetic Acid → HCID 136385896, compound

HRID 1663324Notes

Reaction equation

HRID 1663324 reaction equation
C[O-].[Na+].[C:4]([O:8][C:9]([NH:11][C@@H:12]1[CH2:17][CH2:16][CH2:15][N:14]([C:18]2[N:19]([CH2:31][C:32]#[C:33][CH3:34])[C:20]3[C:25](=[O:26])[N:24]([CH2:27][C:28]#[N:29])[N:23]=[CH:22][C:21]=3[N:30]=2)[CH2:13]1)=[O:10])([CH3:7])([CH3:6])[CH3:5].C(O)(=O)C.[C:39]([OH:48])(=O)[C:40]1[C:41](=[CH:43][CH:44]=[CH:45][CH:46]=1)[NH2:42]>CO>[C:4]([O:8][C:9]([NH:11][C@@H:12]1[CH2:17][CH2:16][CH2:15][N:14]([C:18]2[N:19]([CH2:31][C:32]#[C:33][CH3:34])[C:20]3[C:25](=[O:26])[N:24]([CH2:27][C:28]4[NH:29][C:39](=[O:48])[C:40]5[C:41](=[CH:43][CH:44]=[CH:45][CH:46]=5)[N:42]=4)[N:23]=[CH:22][C:21]=3[N:30]=2)[CH2:13]1)=[O:10])([CH3:7])([CH3:6])[CH3:5]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 227Anthranilic AcidHCID 10942334Sodium MethoxideHCID 86635007HCID 86635007, compound

Product 1

HCID 136385896HCID 136385896, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

40 mg sodium methoxide (95%) are added to a solution of 605 mg 2-[(R)-3-(tert.-butyloxycarbonylamino)-piperidin-1-yl]-3-(2-butyn-1-yl)-5-cyanomethyl-3,5-dihydro-imidazo[4,5-d]pyridazin-4-one in 9 ml of methanol. The mixture is stirred for one hour at ambient temperature and then neutralised with 41 μL glacial acetic acid. Then a solution of 195 mg anthranilic acid in 2 ml of methanol is added and the reaction mixture is heated to 70° C. After about two hours a white, voluminous precipitate is formed and the reaction mixture is cooled to ambient temperature. The precipitate formed is suction filtered, washed with cold methanol and dried.

Workup

  1. temperaturethe reaction mixture is heated to 70° C
  2. customAfter about two hours a white, voluminous precipitate is formed
  3. temperaturethe reaction mixture is cooled to ambient temperature
  4. customThe precipitate formed
  5. filtrationfiltered
  6. washwashed with cold methanol
  7. customdried

Sources & evidence

ORD record
ord-a3430402a15644daa928df6929712384
Source dataset
uspto-grants-2011_10
Patent number
US08034941B2

Reaction notes

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