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Acetonitrile → HCID 20554253, compound

HRID 1277798
Notes
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Reaction equation

HRID 1277798 reaction equation
ClC([O:4][CH3:5])=O.CN1CC[O:10][CH2:9][CH2:8]1.[NH2:13][C:14]1[CH:19]=[CH:18][C:17]([C:20]2[NH:21][C:22](=[O:29])[C:23](=[CH:27][CH:28]=2)[C:24]([OH:26])=[O:25])=[CH:16][CH:15]=1.[Si](Cl)(C)(C)[CH3:31].[CH3:35][C:36]#[N:37]>C(Cl)Cl.C(O)(C)C.CCN(CC)CC>[C:9]([N:13]([C:5](=[O:4])[C:36]([NH2:37])([CH3:31])[CH3:35])[C:14]1[CH:15]=[CH:16][C:17]([C:20]2[NH:21][C:22](=[O:29])[C:23](=[CH:27][CH:28]=2)[C:24]([OH:26])=[O:25])=[CH:18][CH:19]=1)(=[O:10])[CH3:8]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

9

Reactant 5

HCID 6342AcetonitrileHCID 6397ChlorotrimethylsilaneHCID 6586Methyl chloroformateHCID 79724-MethylmorpholineHCID 129189566-(4-Aminophenyl)-1,2-dihydro-2-oxonicotinic acid

Product 1

HCID 20554253HCID 20554253, compound

Reagents, catalysts & solvents

3
HCID 3776IsopropanolSolventHCID 6344DichloromethaneSolventHCID 8471TriethylamineSolvent

Procedure

Methyl chloroformate, 1.7 ml (20 mM), was added to a solution of 2.9 g (20 mM) of alpha-acetamidoisobutyic acid, 2.2 ml (20 mM) of N-methylmorpholine in 50 ml CH3CN at -15° C. The mixture was stirred at -20° C. to -10° C. for 1/2 hr and to it was added in a dropwise manner preformed silylated pyridone solution (by stirring a mixture of 2.3 g (10 mM) of the 6-(4-aminophenyl)-1,2-dihydro-2-oxonicotinic acid, 3.84 ml (30 mM) of Me3SiCl, 4.2 ml (30 mM) of Et3N in 100 ml CH2Cl2 for 40 min) at -10° C. After the addition, the mixture was allowed to stir at 0° C. for 2 hrs and at room temperature for 12 hrs. To the resulting suspension was added 10 ml of isopropanol, stirred for 10 min, and the solids filtered, washed with MeOH, ether, dried to give 2.5 g of 6-[4-(N-acetyl-alpha-amino-isobutyrylamino)phenyl]-1,2-dihydro-2-oxonicotinic acid.

Workup

  1. stirringby stirring
  2. additionAfter the addition
  3. stirringto stir at 0° C. for 2 hrs and at room temperature for 12 hrs
  4. stirringstirred for 10 min
  5. filtrationthe solids filtered
  6. washwashed with MeOH, ether
  7. customdried

Sources & evidence

ORD record
ord-5b54233982004201b26855239acb785e
Source dataset
uspto-grants-1981_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04278681

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes