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4-Methylmorpholine → 8-[3-(Acetylsarcosylamino)-2,6-dichlorobenzyloxy]-2-methylimidazo[1,2-a]pyridine

HRID 1899980
Notes
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Reaction equation

HRID 1899980 reaction equation
C(Cl)(=O)C(C)(C)C.[C:8]([N:11]([CH2:13][C:14]([OH:16])=O)[CH3:12])(=[O:10])[CH3:9].CN1CCOCC1.[NH2:24][C:25]1[C:26]([Cl:44])=[C:27]([C:40]([Cl:43])=[CH:41][CH:42]=1)[CH2:28][O:29][C:30]1[C:31]2[N:32]([CH:36]=[C:37]([CH3:39])[N:38]=2)[CH:33]=[CH:34][CH:35]=1>CN1CCCC1=O>[C:8]([N:11]([CH2:13][C:14]([NH:24][C:25]1[C:26]([Cl:44])=[C:27]([C:40]([Cl:43])=[CH:41][CH:42]=1)[CH2:28][O:29][C:30]1[C:31]2[N:32]([CH:36]=[C:37]([CH3:39])[N:38]=2)[CH:33]=[CH:34][CH:35]=1)=[O:16])[CH3:12])(=[O:10])[CH3:9]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 79724-MethylmorpholineHCID 62493Pivaloyl chlorideHCID 10975514N-Acetyl-N-methylglycineHCID 189235318-[3-Amino-2,6-dichlorobenzyloxy]-2-methylimidazo[1,2-a]pyridine

Product 1

HCID 189232858-[3-(Acetylsarcosylamino)-2,6-dichlorobenzyloxy]-2-methylimidazo[1,2-a]pyridineYield 38.5%

Reagents, catalysts & solvents

1
HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

Pivaloyl chloride (0.22 ml) was added dropwise to a mixture of acetylsarcosine (264 mg), N-methylmorpholine (0.22 ml) and N-methylpyrrolidone (30 ml) under a dry ice-tetrachloromethane bath cooling. This mixture was stirred for 10 minutes under ice-cooling, and 8-[3-amino-2,6-dichlorobenzyloxy]-2-methylimidazo[1,2-a]pyridine (500 mg) was added thereto under a dry ice-tetrachloromethane bath cooling. The mixture was stirred for 22 hours at ambient temperature. The mixture was partitioned between ethyl acetate and a saturated aqueous sodium bicarbonate solution, and the aqueous layer was extracted with ethyl acetate twice. The combined organic layer was dried over magnesium sulfate and concentrated in vacuo, and the residue was purified by flash column chromatography (methylene chloride:methanol=50:1, V/V) to give 8-[3-(acetylsarcosylamino)-2,6-dichlorobenzyloxy]-2-methylimidazo[1,2-a]pyridine (260 mg).

Workup

  1. temperaturecooling
  2. temperaturecooling
  3. temperatureunder a dry ice-tetrachloromethane bath cooling
  4. stirringThe mixture was stirred for 22 hours at ambient temperature
  5. customThe mixture was partitioned between ethyl acetate
  6. extractiona saturated aqueous sodium bicarbonate solution, and the aqueous layer was extracted with ethyl acetate twice
  7. dry with materialThe combined organic layer was dried over magnesium sulfate
  8. concentrationconcentrated in vacuo
  9. customthe residue was purified by flash column chromatography (methylene chloride:methanol=50:1, V/V)

Sources & evidence

ORD record
ord-ecafdda5589042378cc6f1caf8f66b5a
Source dataset
uspto-grants-1996_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05574042

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes