HCID 118036871, compound → HCID 118037033, compound

HRID 1778009Notes

Reaction equation

HRID 1778009 reaction equation
[CH3:1][O:2][CH:3]([O:25][CH3:26])[C:4]1[C:13]([CH2:14][NH:15][CH2:16][CH2:17][S:18][CH2:19][C:20](OCC)=[O:21])=[CH:12][C:11]2[CH2:10][CH2:9][CH2:8][NH:7][C:6]=2[N:5]=1>C1(C)C=CC=CC=1>[CH3:1][O:2][CH:3]([O:25][CH3:26])[C:4]1[C:13]([CH2:14][N:15]2[CH2:16][CH2:17][S:18][CH2:19][C:20]2=[O:21])=[CH:12][C:11]2[CH2:10][CH2:9][CH2:8][NH:7][C:6]=2[N:5]=1

Participants

3

Reactant 1

HCID 118036871HCID 118036871, compound2×

Product 1

HCID 118037033HCID 118037033, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of ethyl 2-((2-(((2-(dimethoxymethyl)-5,6,7,8-tetrahydro-1,8-naphthyridin-3-yl)methyl)amino)ethyl)thio)acetate (intermediate 209, 929 mg, 1.696 mmol) in toluene (5 ml) was stirred at reflux for 20 h. The reaction mixture was concentrated and the crude product was purified using silica gel column chromatography eluting with a gradient of MeOH (0-5%) in DCM. Fractions containing the product were combined and evaporated to yield the title compound as a brown solid. (UPLC-MS 3) tR 0.51 min, ESI-MS 338.3 [M+H]+. 1H NMR (400 MHz, CDCl3) δ 7.15 (s, 1H), 5.16 (s, 1H), 4.74 (s, 2H), 3.57-3.50 (m, 2H), 3.45-3.38 (m, 8H), 3.37 (s, 2H), 2.75 (t, 2H), 2.70 (t, 2H), 1.93-1.84 (m, 2H).

Workup

  1. temperatureat reflux for 20 h
  2. concentrationThe reaction mixture was concentrated
  3. customthe crude product was purified
  4. washeluting with a gradient of MeOH (0-5%) in DCM
  5. additionFractions containing the product
  6. customevaporated

Sources & evidence

ORD record
ord-6fb51f5f7e2543839b7d2b1824f374df
Source dataset
uspto-grants-2016_02
Patent number
US09266883B2

Reaction notes

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