Potassium Phosphate, Tribasic → HCID 118037047, compound

HRID 1778064Notes

Reaction equation

HRID 1778064 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:9](=[N:10][C:11]=1[CH:12]([O:15][CH3:16])[O:13][CH3:14])[NH:8][CH2:7][CH2:6][CH2:5]2.[O:17]1[CH2:21][CH2:20][NH:19][C:18]1=[O:22].[O-]P([O-])([O-])=O.[K+].[K+].[K+].[C@H]1(N)CCCC[C@@H]1N>O1CCOCC1.[Cu]I>[CH3:14][O:13][CH:12]([O:15][CH3:16])[C:11]1[C:2]([N:19]2[CH2:20][CH2:21][O:17][C:18]2=[O:22])=[CH:3][C:4]2[CH2:5][CH2:6][CH2:7][NH:8][C:9]=2[N:10]=1

Participants

7

Reactant 4

HCID 62657Potassium Phosphate, TribasicHCID 739492-OxazolidinoneHCID 4793071,2-Diaminocyclohexane, (+)-HCID 1180362976-Bromo-7-(dimethoxymethyl)-1,2,3,4-tetrahydro-1,8-naphthyridine2×

Product 1

HCID 118037047HCID 118037047, compound

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
120 °C

Procedure

A suspension of 6-bromo-7-(dimethoxymethyl)-1,2,3,4-tetrahydro-1,8-naphthyridine (intermediate 2) (1 g, 3.48 mmol), oxazolidin-2-one (0.364 g, 4.18 mmol), K3PO4 (1.552 g, 7.31 mmol), CuI (0.066 g, 0.348 mmol) and (1S,2S)-cyclohexane-1,2-diamin (0.063 mL, 0.522 mmol) in dioxane (7 ml) was heated to 120° C. for 4 days. Solvents were concentrated and the crude product was purified by silica gel column chromatography eluting with a gradient of MeOH (containing 0.3% of aqueous NH3, 0-10%) in DCM. Product fractions were combined, evaporated and dried to yield the title compound as an orange resin. (UPLC-MS 3) tR 0.44 min; ESI-MS 294.3 [M+H]+. 1H NMR (600 MHz, DMSO-d6) δ 7.14 (s, 1H), 6.83 (s, 1H), 5.12 (s, 1H), 4.39 (dd, 2H), 3.79 (dd, 2H), 3.31-3.19 (m, 8H), 2.69-2.61 (m, 2H), 1.80-1.70 (m, 2H).

Workup

  1. concentrationSolvents were concentrated
  2. customthe crude product was purified by silica gel column chromatography
  3. washeluting with a gradient of MeOH (containing 0.3% of aqueous NH3, 0-10%) in DCM
  4. customevaporated
  5. customdried

Sources & evidence

ORD record
ord-b51188c0229c4ea7b761356d527931d3
Source dataset
uspto-grants-2016_02
Patent number
US09266883B2

Reaction notes

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