Potassium Carbonate → HCID 178487816, compound

HRID 1422932Notes

Reaction equation

HRID 1422932 reaction equation
C(=O)([O-])[O-].[K+].[K+].[NH2:7][C:8]1[C:17]2[C:12](=[CH:13][CH:14]=[C:15]([O:18][CH3:19])[N:16]=2)[N:11]=[CH:10][C:9]=1[OH:20].[CH2:21]([O:28][C:29](=[O:41])[NH:30][C@H:31]1[CH2:36][CH2:35][C@H:34]([C:37](=[O:40])[CH2:38]Br)[CH2:33][CH2:32]1)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>CN(C)C=O>[CH2:21]([O:28][C:29](=[O:41])[NH:30][C@H:31]1[CH2:36][CH2:35][C@H:34]([C:37]2([OH:40])[NH:7][C:8]3[C:17]4[C:12](=[CH:13][CH:14]=[C:15]([O:18][CH3:19])[N:16]=4)[N:11]=[CH:10][C:9]=3[O:20][CH2:38]2)[CH2:33][CH2:32]1)[C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 1363447124-Amino-6-methoxy-[1,5]naphthyridin-3-olHCID 178523765HCID 178523765, compound

Product 1

HCID 178487816HCID 178487816, compoundYield 563.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Potassium carbonate (246 mg, 1.78 mmol, 2.0 eq) is added at room temperature to a stirred solution of 4-amino-6-methoxy-[1,5]naphthyridin-3-ol (170 mg, 0.89 mmol, 1.0 eq) in N,N-dimethylformamide (20 mL), followed by [trans-4-(2-bromo-acetyl)-cyclohexyl]-carbamic acid benzyl ester (315 mg, 0.89 mmol, 1.0 eq). After 4 hours stirring at room temperature, solvent is evaporated and the residue is extracted with ethyl acetate (3×20 mL) and a saturated ammonium chloride aqueous solution (20 mL). The combined organic layers are dried over sodium sulfate, filtered and concentrated to afford [trans-4-(3-hydroxy-6-methoxy-3,4-dihydro-2H-1-oxa-4,5,9-triaza-phenanthren-3-yl)-cyclohexyl]-carbamic acid benzyl ester (2.33 g, 88% Yield).

Workup

  1. customsolvent is evaporated
  2. extractionthe residue is extracted with ethyl acetate (3×20 mL)
  3. dry with materialThe combined organic layers are dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-56c449315b0f4de188f0b240fa9cae05
Source dataset
uspto-grants-2015_01
Patent number
US08927541B2

Reaction notes

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