2-(Dimethoxymethyl)-5,6,7,8-tetrahydro-1,8-naphthyridine-3-carbaldehyde → HCID 118036368, compound

HRID 1777996Notes

Reaction equation

HRID 1777996 reaction equation
[CH3:1][O:2][CH:3]([O:16][CH3:17])[C:4]1[C:13]([CH:14]=[O:15])=[CH:12][C:11]2[CH2:10][CH2:9][CH2:8][NH:7][C:6]=2[N:5]=1.[CH3:18][Mg+].[Br-]>C1COCC1>[CH3:17][O:16][CH:3]([O:2][CH3:1])[C:4]1[C:13]([CH:14]([OH:15])[CH3:18])=[CH:12][C:11]2[CH2:10][CH2:9][CH2:8][NH:7][C:6]=2[N:5]=1

Participants

4

Reactant 2

HCID 1180364262-(Dimethoxymethyl)-5,6,7,8-tetrahydro-1,8-naphthyridine-3-carbaldehyde2×HCID 178418689HCID 178418689, compound2×

Product 1

HCID 118036368HCID 118036368, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 2-(dimethoxymethyl)-5,6,7,8-tetrahydro-1,8-naphthyridine-3-carbaldehyde (intermediate 41, 13.5 g, 49.7 mmol) in THF (250 ml) at 0° C. was slowly added a solution of MeMgBr (3M in diethylether, 66.3 ml, 199 mmol) in THF (250 ml). The reaction mixture was allowed to warm to room temperature and stirred 3 h. Additional MeMgBr (16.6 ml, 49.7 mmol) was added at room temperature and the reaction mixture was stirred for approximately 30 minutes. The reaction mixture was quenched with saturated aqueous NH4Cl solution (150 ml) and water (100 ml) and extracted with EtOAc (2×). The combined organic phases were dried using Na2SO4, filtered and concentrated to yield the title compound as a yellow solid. (UPLC-MS 3) tR 0.44 min, ESI-MS 253.1 [M+H]+. 1H NMR (600 MHz, DMSO-d6) δ 7.33 (s, 1H), 6.36 (s, 1H), 5.18-5.10 (m, 1H), 5.03 (s, 1H), 4.65 (d, 1H), 3.31-3.26 (m, 6H), 3.26-3.21 (m, 2H), 2.69-2.62 (m, 2H), 1.82-1.71 (m, 2H), 1.20 (d, 3H).

Workup

  1. stirringthe reaction mixture was stirred for approximately 30 minutes
  2. customThe reaction mixture was quenched with saturated aqueous NH4Cl solution (150 ml) and water (100 ml)
  3. extractionextracted with EtOAc (2×)
  4. customThe combined organic phases were dried
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-d00ec9b5ea6f4fae9eedaaa70ca97ecf
Source dataset
uspto-grants-2016_02
Patent number
US09266883B2

Reaction notes

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