Hydrochloric Acid → HCID 66826339, compound

HRID 2177956Notes

Reaction equation

HRID 2177956 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-ab48a472603d41b5a2cd3cf205b6172c
Source dataset
uspto-grants-2015_06
Patent number
US09067893B2

Reaction notes

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