Hydrochloric Acid → HCID 22219469, compound

HRID 395279Notes

Reaction equation

HRID 395279 reaction equation
Cl.[NH2:2][C:3]1[C:4](=[O:14])[NH:5][C:6](=[O:13])[N:7]([CH2:10][CH2:11][CH3:12])[C:8]=1[NH2:9].C[O:16][C:17]([C:19]12[CH2:26][CH2:25][C:22]([C:27](O)=O)([CH2:23][CH2:24]1)[CH2:21][CH2:20]2)=[O:18].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(CC)CC.O.[OH-].[Na+].Cl>CN(C=O)C>[O:13]=[C:6]1[N:7]([CH2:10][CH2:11][CH3:12])[C:8]2[N:9]=[C:27]([C:22]34[CH2:25][CH2:26][C:19]([C:17]([OH:18])=[O:16])([CH2:20][CH2:21]3)[CH2:24][CH2:23]4)[NH:2][C:3]=2[C:4](=[O:14])[NH:5]1

Participants

9

Reactant 7

HCID 313Hydrochloric AcidHCID 962WaterHCID 8471TriethylamineHCID 14798Sodium HydroxideHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 110420624-(Methoxycarbonyl)bicyclo[2.2.2]octane-1-carboxylic acidHCID 11994282HCID 11994282, compound

Product 1

HCID 22219469HCID 22219469, compoundYield 80.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

5,6-Diamino-1-propyl-1H-pyrimidine-2,4-dione hydrochloride salt (570 mg) was dissolved in 20 mL of DMF along with bicyclo[2.2.2]octane-1,4-dicarboxylic acid monomethyl ester (520 mg, 2.45 mmol). HATU (980 mg, 1.05 eq) was added, followed by Et3N (1.40 mL, 4.05 eq). The resulting reaction mixture was stirred at rt overnight. The following morning, the reaction mixture was filtered to remove some of the precipitate. The filtrate was concentrated under reduced pressure. The resulting residue was dissolved in 10 mL of H2O containing 10 eq of NaOH (980 mg). The reaction mixture was stirred under reflux for 2 h. It was then cooled to rt and acidified to pH2 with concentrated HCl. The resulting precipitate was collected by filtration and dried to afford 680 mg of the acid derivative.

Workup

  1. customThe resulting reaction mixture
  2. filtrationThe following morning, the reaction mixture was filtered
  3. customto remove some of the precipitate
  4. concentrationThe filtrate was concentrated under reduced pressure
  5. stirringThe reaction mixture was stirred
  6. temperatureunder reflux for 2 h
  7. temperatureIt was then cooled to rt
  8. filtrationThe resulting precipitate was collected by filtration
  9. customdried

Sources & evidence

ORD record
ord-add3e5f84e094e36af9db618b3beebae
Source dataset
uspto-grants-2003_08
Patent number
US06605601B2

Reaction notes

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