Hydrochloric Acid → HCID 66826339, compound

HRID 924862Notes

Reaction equation

HRID 924862 reaction equation
CS([O:5][C:6]1[C:11]([N+:12]([O-:14])=[O:13])=[CH:10][C:9]([CH:15]2[C:20]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)=[C:19]([C:27]3[CH:32]=[CH:31][C:30]([NH:33][S:34]([CH3:37])(=[O:36])=[O:35])=[CH:29][CH:28]=3)[NH:18][C:17](=[O:38])[NH:16]2)=[CH:8][C:7]=1[O:39][CH2:40][CH3:41])(=O)=O.[OH-].[Na+].Cl.O>C(O)C>[CH2:40]([O:39][C:7]1[CH:8]=[C:9]([CH:15]2[NH:16][C:17](=[O:38])[NH:18][C:19]([C:27]3[CH:28]=[CH:29][C:30]([NH:33][S:34]([CH3:37])(=[O:35])=[O:36])=[CH:31][CH:32]=3)=[C:20]2[C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH:10]=[C:11]([N+:12]([O-:14])=[O:13])[C:6]=1[OH:5])[CH3:41]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 86669335HCID 86669335, compound

Product 1

HCID 66826339HCID 66826339, compoundYield 68.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

To a mixture of 2-ethoxy-4-(6-(4-(methylsulfonamido)phenyl)-2-oxo-5-phenyl-1,2,3,4-tetrahydropyrimidin-4-yl)-6-nitrophenyl methanesulfonate (60 mg, 0.10 mmol) in ethanol (2 mL) was added sodium hydroxide aqueous solution (2 mL, 1.25 mol/L) at 0° C. The mixture was heated at 80° C. for 5 h, cooled down to room temperature, adjusted to pH=5 with diluted hydrochloric acid, poured into water (20 mL), and extracted with ethyl acetate (30 mL). The organic layer was washed with brine (5 mL), dried over anhydrous sodium sulfate, and evaporated. The residue was purified by preparative HPLC to give Compound 101 (36.0 mg, yield 68.9%). HNMR (DMSO-d6 300 MHz): δ 10.34 (s, 1H), 9.91 (s, 1H), 8.73 (s, 1H), 7.59 (s, 1H), 7.49 (s, 1H), 7.23 (d, J=9.0 Hz, 3H), 7.12-7.06 (m, 5H), 6.90 (d, J=6.9 Hz, 2H), 5.24 (d, J=2.7 Hz, 1H), 4.12-4.08 (m, 2H), 3.04 (s, 3H), 1.42-1.37 (m, 3H); MS (ESI): m/z 525.0 [M+H]+.

Workup

  1. temperaturecooled down to room temperature
  2. extractionextracted with ethyl acetate (30 mL)
  3. washThe organic layer was washed with brine (5 mL)
  4. dry with materialdried over anhydrous sodium sulfate
  5. customevaporated
  6. customThe residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-b733ebb394a641dc8f7689aef4e323a3
Source dataset
uspto-grants-2016_03
Patent number
US09283229B2

Reaction notes

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