Hydrochloric Acid → HCID 59160593, compound

HRID 1500054Notes

Reaction equation

HRID 1500054 reaction equation
[CH:1]1([C:6]([O:8][CH2:9][O:10][C:11]2[N:16]=[C:15](/[N:17]=[CH:18]/N(C)C)[C:14]([F:22])=[CH:13][N:12]=2)=[O:7])[CH2:5][CH2:4][CH2:3][CH2:2]1.Cl.C([O-])(O)=[O:25].[Na+]>O1CCOCC1>[CH:1]1([C:6]([O:8][CH2:9][O:10][C:11]2[N:16]=[C:15]([NH:17][CH:18]=[O:25])[C:14]([F:22])=[CH:13][N:12]=2)=[O:7])[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 313Hydrochloric Acid2×HCID 516892Sodium BicarbonateHCID 178484254HCID 178484254, compound

Product 1

HCID 59160593HCID 59160593, compoundYield 95.4%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A 25 mL vial was charged with (E)-(4-((dimethylamino)methyleneamino)-5-fluoropyrimidin-2-yloxy)methyl cyclopentanecarboxylate (50.0 mg, 0.161 mmol), 1,4-dioxane (4 mL), and 1.0 M aqueous HCl (78 μL, 0.078 mmol) and was agitated on an orbital shaker for 5 h. The reaction was monitored by ultra performance liquid chromatography (UPLC) and determined to be incomplete, therefore an additional portion of 1.0 M aqueous HCl (78 μL, 0.078 mmol) was added. After 1 h, the reaction was quenched by the addition of 1.0 M aqueous NaHCO3 (260 μL, 0.260 mmol) and concentrated under reduced pressure at 45° C. The dried residue was then extracted with EtOAc (5 mL×4), and concentrated to dryness under reduced pressure to obtain (5-fluoro-4-formamidopyrimidin-2-yloxy)methyl cyclopentanecarboxylate (43.5 mg, 95%) as a white solid: mp 76-79° C.; 1H NMR (300 MHz, DMSO-d6) δ 11.38 (bs, 1H), 9.31 (d, J=5.7 Hz, 1H), 8.52 (d, J=2.6 Hz, 1H), 5.97 (s, 2H), 2.71-2.85 (m, 1H), 1.40-1.89 (m, 8H); MS (ESI) m/z 306 (M+Na)+, 282 (M−H)−.

Workup

  1. waitAfter 1 h
  2. concentrationconcentrated under reduced pressure at 45° C
  3. extractionThe dried residue was then extracted with EtOAc (5 mL×4)
  4. concentrationconcentrated to dryness under reduced pressure

Sources & evidence

ORD record
ord-8391e9abb5d84bc8a558fa9e36328225
Source dataset
uspto-grants-2015_12
Patent number
US09204653B2

Reaction notes

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