6-Methylnicotinic acid → HCID 68887733, compound

HRID 857902Notes

Reaction equation

HRID 857902 reaction equation
C[C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=O)=[CH:4][N:3]=1.[CH2:11]([O:13][C:14]([CH:16]1[NH:21][CH2:20][CH2:19][N:18]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:17]1)=[O:15])[CH3:12].Cl.[CH3:30]N(C)CCCN=C=NCC>ClCCl.CN(C)C1C=CN=CC=1.CN(C1C=CC=CN=1)C>[CH2:11]([O:13][C:14]([CH:16]1[N:21]([C:6]([C:5]2[CH:4]=[N:3][CH:2]=[CH:10][C:9]=2[CH3:30])=[O:8])[CH2:20][CH2:19][N:18]([C:22]([O:24][C:25]([CH3:27])([CH3:26])[CH3:28])=[O:23])[CH2:17]1)=[O:15])[CH3:12]

Participants

7

Reactant 3

HCID 1378606-Methylnicotinic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 114026711-tert-Butyl 3-ethyl piperazine-1,3-dicarboxylate

Product 1

HCID 68887733HCID 68887733, compound

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 218852-DimethylaminopyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

A stirred suspension of 6-methylnicotinic acid (29 g) in dry dichloromethane (400 mL) was treated with piperazine-1,3-dicarboxylic acid 1-tert-butyl ester 3-ethyl ester (57.58 g, prepared according to the procedure described in WO 96/31478 Step B page 94), then with 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (40.7 g). After stirring at room temperature for a further 1 hour the reaction mixture was treated with 4-dimethylaminopyridine (3.00 g) and stirring continued overnight. The reaction mixture was then further treated with dimethylaminopyridine (1.00 g). After stirring for a further 7 hours the reaction mixture was washed with a saturated aqueous solution of sodium hydrogen carbonate and then water. The organic phase was dried over magnesium sulfate and evaporated. The residue was subjected to column chromatography on silica eluting with a mixture of ethyl acetate and pentane (2:1, v/v) to give the title compound (54.0 g) as a yellow oil, Rf 0.31 (ethyl acetate).

Workup

  1. customprepared
  2. stirringstirring continued overnight
  3. stirringAfter stirring for a further 7 hours the reaction mixture
  4. washwas washed with a saturated aqueous solution of sodium hydrogen carbonate
  5. dry with materialThe organic phase was dried over magnesium sulfate
  6. customevaporated
  7. additionThe residue was subjected to column chromatography on silica eluting with a mixture of ethyl acetate and pentane (2:1

Sources & evidence

ORD record
ord-7254a8b4cc2248a58721b501f0e95eec
Source dataset
uspto-grants-2006_12
Patent number
US07148215B2

Reaction notes

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