Potassium Phosphate, Tribasic → HCID 118036572, compound

HRID 1778062Notes

Reaction equation

HRID 1778062 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.[NH:17]1[CH2:22][CH2:21][O:20][CH2:19][C:18]1=[O:23].[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:17]2[CH2:22][CH2:21][O:20][CH2:19][C:18]2=[O:23])=[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 669533-MorpholinoneHCID 4793071,2-Diaminocyclohexane, (+)-HCID 1180362976-Bromo-7-(dimethoxymethyl)-1,2,3,4-tetrahydro-1,8-naphthyridine2×

Product 1

HCID 118036572HCID 118036572, 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 12, 1 g, 3.48 mmol), morpholin-3-one (0.423 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 (1-3%) in DCM. Product fractions were combined, evaporated and dried to yield the title compound as an orange resin. (UPLC-MS 3) tR 0.43 min; ESI-MS 308.2 [M+H]+.

Workup

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

Sources & evidence

ORD record
ord-bb71876a325147f69ff2ef973d643566
Source dataset
uspto-grants-2016_02
Patent number
US09266883B2

Reaction notes

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