Dimethylacetamide → HCID 25119787, compound

HRID 1697094Notes

Reaction equation

HRID 1697094 reaction equation
[CH3:1][O:2][C:3]([C:5]1[N:6]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[C:7]2[C:12]([C:13](=[O:25])[C:14]=1[CH2:15][C:16]1[CH:17]=[N:18][C:19]([C:22](O)=[O:23])=[CH:20][CH:21]=1)=[CH:11][CH:10]=[C:9]([CH3:26])[N:8]=2)=[O:4].F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)[N:51]([CH3:53])[CH3:52])C2C=CC=CC=2N=N1.CC(N(C)C)=O.CCN(C(C)C)C(C)C>C1COCC1.O.CCOC(C)=O>[CH3:1][O:2][C:3]([C:5]1[N:6]([C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=2)[C:7]2[C:12]([C:13](=[O:25])[C:14]=1[CH2:15][C:16]1[CH:17]=[N:18][C:19]([C:22](=[O:23])[N:51]([CH3:53])[CH3:52])=[CH:20][CH:21]=1)=[CH:11][CH:10]=[C:9]([CH3:26])[N:8]=2)=[O:4]

Participants

8

Reactant 4

HCID 31374Dimethylacetamide2×HCID 81531Diisopropylethylamine2×HCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphate2×HCID 66816229HCID 66816229, compound

Product 1

HCID 25119787HCID 25119787, compoundYield 79.2%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To 3-(6-carboxy-pyridin-3-ylmethyl)-7-methyl-4-oxo-1-phenyl-1,4-dihydro-[1,8]naphthyridine-2-carboxylic acid methyl ester (0.095 g) in THF (6 mL) was added BOP (0.11 g), followed by DMA (0.15 mL, 2M in THF) and Hunig's Base (ethyl-diisopropylamine) (0.042 mL). Solids began to precipitate: DCM was added until all solids dissolved, and a homogenous reaction mixture was obtained. The mixture was stirred at RT for 1 h, then an additional aliquot of BOP, Hunig's base, and DMA added, and the mixture stirred at RT overnight. The product was worked up with EtOAc and H2O, washed with NaHCO3 (aq) and H2O, and dried over MgSO4. The product was concentrated, applied to a silica gel column with EtOAc, and eluted with EtOAc/MeOH, and concentrated to yield 3-(6-dimethylcarbamoyl-pyridin-3-ylmethyl)-7-methyl-4-oxo-1-phenyl-1,4-dihydro[1,8]naphthyridine-2-carboxylic acid methyl ester (compound 103) (80 mg) as a pale yellow solid. M+H=457; mp=235.0-236.0° C.

Workup

  1. customto precipitate
  2. additionDCM was added until all solids
  3. dissolutiondissolved
  4. customa homogenous reaction mixture was obtained
  5. stirringthe mixture stirred at RT overnight
  6. washwashed with NaHCO3 (aq) and H2O
  7. dry with materialdried over MgSO4
  8. concentrationThe product was concentrated
  9. washeluted with EtOAc/MeOH
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-8cd215f1e84243eda7cc401c307a2927
Source dataset
uspto-grants-2012_04
Patent number
US08163906B2

Reaction notes

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