D-Lactic Acid → HCID 60142906, compound

HRID 925512Notes

Reaction equation

HRID 925512 reaction equation
Cl.[CH3:2][O:3][C:4]1[N:9]=[CH:8][C:7]([C:10]2[CH:19]=[CH:18][C:17]3[N:16]=[CH:15][C:14]4[CH2:20][N:21]([CH3:31])[C:22](=[O:30])[N:23]([CH:24]5[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]5)[C:13]=4[C:12]=3[N:11]=2)=[CH:6][CH:5]=1.[C:32](O)(=[O:36])[C@@H:33]([CH3:35])[OH:34].ON1C2C=CC=CC=2N=N1.Cl.C(N=C=NCCCN(C)C)C>CO.ClCCl.C(N(CC)CC)C>[OH:34][C@H:33]([CH3:35])[C:32]([N:27]1[CH2:28][CH2:29][CH:24]([N:23]2[C:13]3[C:12]4[N:11]=[C:10]([C:7]5[CH:8]=[N:9][C:4]([O:3][CH3:2])=[CH:5][CH:6]=5)[CH:19]=[CH:18][C:17]=4[N:16]=[CH:15][C:14]=3[CH2:20][N:21]([CH3:31])[C:22]2=[O:30])[CH2:25][CH2:26]1)=[O:36]

Participants

8

Reactant 4

HCID 61503D-Lactic AcidHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 90449331HCID 90449331, compound2×

Product 1

HCID 60142906HCID 60142906, compoundYield 81.4%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent2×HCID 8471TriethylamineSolvent

Procedure

9-(6-methoxypyridin-3-yl)-3-methyl-1-(piperidin-4-yl)-3,4-dihydropyrimido[5,4-c][1,5]naphthyridin-2(1H)-one hydrochloride (hydrochloride of Compound 114 (100 mg, 0.227 mmol)) and triethylamine (0.177 mL) were added to dichloromethane (20 mL), stirred at room temperature for 0.5 h, then to the system sequentially added (R)-lactic acid (26.7 mg, 0.296 mmol), 1-hydroxybenzotriazole (37.8 mg, 0.280 mmol) and 1-ethyl-(3-dimethylaminopropyl)carbodiimide hydrochloride (70.8 mg, 0.37 mmol). The reaction mixture was stirred at room temperature for 2 h. After confirming the reaction was completed by a thin layer chromatography plate (dichloromethane:methanol=10:1), the reaction liquid was washed sequentially with a saturated aqueous solution of sodium carbonate, water and saturated brine, and the organic layer was dried over anhydrous sodium sulfate, concentrated and subjected to silica gel column chromatography (dichloromethane:methanol=10:1) to give 88 mg of a white solid.

Workup

  1. stirringThe reaction mixture was stirred at room temperature for 2 h
  2. customthe reaction liquid
  3. washwas washed sequentially with a saturated aqueous solution of sodium carbonate, water and saturated brine
  4. dry with materialthe organic layer was dried over anhydrous sodium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-b26a739304884964a17c89173097e51a
Source dataset
uspto-grants-2016_03
Patent number
US09284315B2

Reaction notes

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