Hydrochloric Acid → 8-[2-(cyclopropylmethoxy)-5-ethylsulfonylphenyl]-6-methyl-3,4,4a,8a-tetrahydro-2H-pyrido[4,3-b][1,4]oxazin-5-one

HRID 575800Notes

Reaction equation

HRID 575800 reaction equation
[CH:1]1([CH2:4][O:5][C:6]2[CH:11]=[CH:10][C:9]([S:12]([CH2:15][CH3:16])(=[O:14])=[O:13])=[CH:8][C:7]=2[C:17]2[C:22]3[O:23][CH2:24][C:25](=O)[NH:26][C:21]=3[C:20](=[O:28])[N:19]([CH3:29])[CH:18]=2)[CH2:3][CH2:2]1.[H-].[H-].[H-].[H-].[Li+].[Al+3].Cl.C([O-])(O)=O.[Na+]>C1COCC1.CC(=O)OCC.CO.O>[CH:1]1([CH2:4][O:5][C:6]2[CH:11]=[CH:10][C:9]([S:12]([CH2:15][CH3:16])(=[O:13])=[O:14])=[CH:8][C:7]=2[C:17]2[CH:22]3[O:23][CH2:24][CH2:25][NH:26][CH:21]3[C:20](=[O:28])[N:19]([CH3:29])[CH:18]=2)[CH2:3][CH2:2]1

Participants

9

Reactant 4

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 21226445Aluminium lithium hydrideHCID 118023002US10023592, Example 365

Product 1

HCID 1180217468-[2-(cyclopropylmethoxy)-5-ethylsulfonylphenyl]-6-methyl-3,4,4a,8a-tetrahydro-2H-pyrido[4,3-b][1,4]oxazin-5-one

Reagents, catalysts & solvents 4

HCID 887MethanolSolvent2×HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent3×

Procedure

The title compound of Example 365, step 3 in anhydrous THF was treated with excess 1M LAH in THF at room temperature. After about 30 min, ice, water, methanol and 1M HCl were added followed by saturated aqueous NaHCO3 and EA extractive work up. Silica gel chromatography (EA, followed by 5% methanol in EA) gave the title compound as a clear glass. 1H NMR: (DMSO-d6, 400 MHz) δ ppm 0.32 (br. s., 2H) 0.54 (br. s., 2H) 1.03-1.30 (m, 4H) 3.45 (br. s., 3H) 3.94 (br. s., 2H) 4.09 (br. s., 2H) 5.03 (br. s., 1H) 7.05 (br. s., 1H) 7.22 (br. s., 1H) 7.62 (br. s., 1H) 7.78 (br. s., 1H). 1H NMR: (DMSO-d6/DCl, 400 MHz) δ ppm 0.29 (br. s., 2H) 0.55 (br. s., 2H) 1.10 (br. s., 4H) 3.25 (br. s., 2H) 3.45 (br. s., 2H) 3.51 (br. s., 3H) 3.93 (br. s., 2H) 4.43 (br. s., 2H) 7.27 (br. s., 1H) 7.69 (br. s., 1H) 7.84 (br. s., 2H). LCMS: 405 (M+H)+

Sources & evidence

ORD record
ord-0890348c6cf64a028cf39e63aad0a3cd
Source dataset
uspto-grants-2015_05
Patent number
US09034900B2

Reaction notes

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