3-Methoxypropylamine → HCID 44632862, compound

HRID 550874Notes

Reaction equation

HRID 550874 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]([NH:9][C:10]12[CH2:19][CH:14]3[CH2:15][CH:16]([CH2:18][C:12]([NH:20][C:21]([C:23]4[CH:28]=[CH:27][CH:26]=[C:25](Cl)[N:24]=4)=[O:22])([CH2:13]3)[CH2:11]1)[CH2:17]2)=[O:8].[CH3:30][O:31][CH2:32][CH2:33][CH2:34][NH2:35].C(=O)([O-])[O-].[Cs+].[Cs+]>[Cu]=O.CC(N(C)C)=O>[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]([NH:9][C:10]12[CH2:19][CH:14]3[CH2:15][CH:16]([CH2:18][C:12]([NH:20][C:21]([C:23]4[CH:28]=[CH:27][CH:26]=[C:25]([NH:35][CH2:34][CH2:33][CH2:32][O:31][CH3:30])[N:24]=4)=[O:22])([CH2:13]3)[CH2:11]1)[CH2:17]2)=[O:8]

Participants

6

Reactant 3

HCID 16723-MethoxypropylamineHCID 10796Cesium carbonateHCID 59161108HCID 59161108, compound2×

Product 1

HCID 44632862HCID 44632862, compound

Reagents, catalysts & solvents 2

HCID 14829Copper oxideCatalystHCID 31374DimethylacetamideSolvent

Conditions

Temperature
230 °C

Procedure

To a microwave vial was added a stir bar, 6-chloro-pyridine-2-carboxylic acid {3-[(pyridine-2-carbonyl)-amino]-adamantan-1-yl}-amide (Intermediate 4, 20 mg, 0.05 mmol), copper (II) oxide (20 mg, 0.2 mmole), DMA (1 mL), 3-methoxy-propylamine (0.05 mL) and cesium carbonate (120 mg, 0.3 mmol). The mixture was heated at 230° C. under microwave irradiation for 30 min. Solvent was removed in Genevac. The residue was dissolved in DCM (2 mL), washed with aq. 1 N NaOH (2 mL), and water (2×2 mL). After removing the solvent, the crude product was purified on a RP-HPLC/MS system (Gradient: acetonitrile in water with a cycle time of 5 min. Flow rate: 100 mL/min. Mobile phase additive: 25 mM of ammonium acetate. Column: Inertsil® C8, 30×50 mm, 5 μm particle size (GL Sciences, Tokyo, Japan)) to afford 3.9 mg of the title compound, 6-(3-methoxy-propylamino)-pyridine-2-carboxylic acid {3-[(pyridine-2-carbonyl)-amino]-adamantan-1-yl}-amide. The product was quality checked (QC) by LC-MS (Gradient: acetonitrile in water, 30-90%, in 1.7 minutes with a cycle time of 2 min. Flow rate: 5.0 mL/min. Mobile phase additive: 30 mM of ammonium formate. Column: Inertsil® C8, 50×4.6 mm, 3 μm particle size (GL Sciences, Tokyo, Japan)): Retention time: 1.29 min; purity (UV254): 94%; ESI-MS m/z: 464.6 (M+H)+.

Workup

  1. additionTo a microwave vial was added a stir bar
  2. customSolvent was removed in Genevac
  3. dissolutionThe residue was dissolved in DCM (2 mL)
  4. washwashed with aq. 1 N NaOH (2 mL), and water (2×2 mL)
  5. customAfter removing the solvent
  6. customthe crude product was purified on a RP-HPLC/MS system (Gradient
  7. customwith a cycle time of 5 min

Sources & evidence

ORD record
ord-46ef40b948ff4439a8a2576810404673
Source dataset
uspto-grants-2011_05
Patent number
US07947680B2

Reaction notes

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