Triethylamine → HCID 46940978, compound

HRID 1959953Notes

Reaction equation

HRID 1959953 reaction equation
C[N:2]1[C:11]2[C:6](=[CH:7][N:8]=[CH:9][C:10]=2[C:12]2[CH:17]=[CH:16][C:15]([O:18][CH2:19][CH2:20][O:21][CH:22]3[CH2:27][CH2:26][O:25][CH2:24][CH2:23]3)=[CH:14][CH:13]=2)[CH:5]=[CH:4][CH:3]1[C:28]([OH:30])=O.Cl.CN.[CH2:34]([N:36](CC)CC)C.ON1C2C=CC=CC=2N=N1.Cl.C(N=C=NCCCN(C)C)C>CN(C)C=O>[CH3:34][NH:36][C:28]([C:3]1[CH:4]=[CH:5][C:6]2[C:11](=[C:10]([C:12]3[CH:17]=[CH:16][C:15]([O:18][CH2:19][CH2:20][O:21][CH:22]4[CH2:27][CH2:26][O:25][CH2:24][CH2:23]4)=[CH:14][CH:13]=3)[CH:9]=[N:8][CH:7]=2)[N:2]=1)=[O:30]

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 6364545Methylamine hydrochlorideHCID 66730410HCID 66730410, compound

Product 1

HCID 46940978HCID 46940978, compoundYield 10.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

N-methyl-8-{4-[2-(tetrahydro-2H-pyran-4-yloxy)ethoxy]phenyl}-1,6-naphthyridine-2-carboxylic acid (281 mg, 0.71 mmol), an intermediate product of the synthetic process in Example 9 (9a), was dissolved in N,N-dimethylformamide (7 mL), to which methylamine hydrochloride (478 mg, 7.13 mol), triethylamine (1.2 mL, 8.56 mmol), 1-hydroxybenzotriazole (33 mg, 0.21 mmol), and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (681 mg, 3.56 mmol) were added, followed by stirring at room temperature for 48 hours. The resulting reaction liquid was filtered and concentrated under reduced pressure. The residue thus obtained was purified by silica gel column chromatography (hexane:ethyl acetate, 40:60-0:100, V/V) to give the desired title compound (30 mg, yield 10%).

Workup

  1. additionwere added
  2. customThe resulting reaction liquid
  3. filtrationwas filtered
  4. concentrationconcentrated under reduced pressure
  5. customThe residue thus obtained
  6. customwas purified by silica gel column chromatography (hexane:ethyl acetate, 40:60-0:100, V/V)

Sources & evidence

ORD record
ord-b143e5c11bdd48088b0fa19b4beb743a
Source dataset
uspto-grants-2013_04
Patent number
US08410273B2

Reaction notes

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