Water → HCID 117667741, compound

HRID 712693Notes

Reaction equation

HRID 712693 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7]2[CH:8]=[C:9]3[C:14](=[N:15][CH:16]=2)[NH:13][CH2:12][CH2:11][CH2:10]3)[CH:2]=1.[CH3:17][N:18]=[C:19]=[O:20].CCN(CC)CC.O>C1COCC1>[CH3:17][NH:18][C:19]([N:13]1[C:14]2[C:9](=[CH:8][C:7]([C:3]3[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=3)=[CH:16][N:15]=2)[CH2:10][CH2:11][CH2:12]1)=[O:20]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 12228Methyl IsocyanateHCID 117667315HCID 117667315, compound

Product 1

HCID 117667741HCID 117667741, compoundYield 45.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 6-pyridin-3-yl-1,2,3,4-tetrahydro-[1,8]naphthyridine (40 mg, 0.19 mmol) in 2 mL of THF is added to methyl isocyanate (16 mg, 0.28 mmol) followed by the addition of Et3N (61 mg, 0.60 mmol). The mixture is stirred at ambient temperature for 16 hrs. To the mixture is added 0.5 mL of water, stirred for 5 minutes and concentrated in vacuo. The residue is dissolved in 1 mL of DMF, filtered and purified by reverse phase HPLC to give 23 mg of the titled product.

Workup

  1. stirringstirred for 5 minutes
  2. concentrationconcentrated in vacuo
  3. dissolutionThe residue is dissolved in 1 mL of DMF
  4. filtrationfiltered
  5. custompurified by reverse phase HPLC

Sources & evidence

ORD record
ord-8f264b64d1d04efdabe1475d966c9546
Source dataset
uspto-grants-2015_11
Patent number
US09181272B2

Reaction notes

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