Dichloromethane → HCID 60142906, compound

HRID 2200862Notes

Reaction equation

HRID 2200862 reaction equation
C(Cl)Cl.Cl.[CH3:5][O:6][C:7]1[N:12]=[CH:11][C:10]([C:13]2[CH:22]=[CH:21][C:20]3[N:19]=[CH:18][C:17]4[CH2:23][N:24]([CH3:34])[C:25](=[O:33])[N:26]([CH:27]5[CH2:32][CH2:31][NH:30][CH2:29][CH2:28]5)[C:16]=4[C:15]=3[N:14]=2)=[CH:9][CH:8]=1.[C:35](O)(=[O:39])[C@@H:36]([CH3:38])[OH:37].ON1C2C=CC=CC=2N=N1>C(Cl)Cl.CO.C(N(CC)CC)C>[OH:37][C@H:36]([CH3:38])[C:35]([N:30]1[CH2:31][CH2:32][CH:27]([N:26]2[C:16]3[C:15]4[N:14]=[C:13]([C:10]5[CH:11]=[N:12][C:7]([O:6][CH3:5])=[CH:8][CH:9]=5)[CH:22]=[CH:21][C:20]=4[N:19]=[CH:18][C:17]=3[CH2:23][N:24]([CH3:34])[C:25]2=[O:33])[CH2:28][CH2:29]1)=[O:39]

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 61503D-Lactic AcidHCID 757711-HydroxybenzotriazoleHCID 90449331HCID 90449331, compound2×

Product 1

HCID 60142906HCID 60142906, compoundYield 81.4%

Reagents, catalysts & solvents 2

HCID 8471TriethylamineSolventHCID 21226129Dichloromethane methanolSolvent

Procedure

To DCM (20 mL) were added 9-(6-methoxypyridin-3-yl)-3-methyl-1-(piperidin-4-yl)-3,4-dihydropyrimido[5,4-c][1,5]naphthyridin-2(1H)-one hydrochloride salt (Compound 1) (100 mg, 0.227 mmol) and triethylamine (0.177 mL). The mixture was stirred at ambient temperature for 0.5 h. Then to the mixture were sequentially added (R)-lactic acid (26.7 mg, 0.296 mmol), 1-hydroxybenzotriazole (37.8 mg, 0.280 mmol) and 1-ethyl-(3-dimethyllaminopropyl)carbodiimide hydrochloride (70.8 mg, 0.37 mmol). The reaction mixture was stirred at ambient temperature for 2 h, and the completion of the reaction was indicated by TLC (DCM/methanol=10/1). The reaction mixture was washed sequentially with saturated aqueous sodium carbonate, water and brine. The organic phase was dried over sodium sulfate, concentrated and purified by silica gel column chromatography (DCM/methanol=10/1) to give a white solid (88 mg, 81.4% yield).

Workup

  1. stirringThe reaction mixture was stirred at ambient temperature for 2 h
  2. washThe reaction mixture was washed sequentially with saturated aqueous sodium carbonate, water and brine
  3. dry with materialThe organic phase was dried over sodium sulfate
  4. concentrationconcentrated
  5. custompurified by silica gel column chromatography (DCM/methanol=10/1)

Sources & evidence

ORD record
ord-f335440baa5241bdab3d261d649c6b6b
Source dataset
uspto-grants-2016_06
Patent number
US09359371B2

Reaction notes

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