Hydrochloric Acid → HCID 20434941, compound

HRID 1154315Notes

Reaction equation

HRID 1154315 reaction equation
[BH4-].[Na+].[CH3:3][O:4][C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][C:14]=1[O:15][CH3:16])[N:11]=[CH:10][N:9]=[C:8]2[N:17]1[CH2:22][CH2:21][CH:20]([CH:23]([CH3:34])[CH2:24][N:25]2[CH:30]=[CH:29][C:28]([CH3:31])=[N:27][S:26]2(=[O:33])=[O:32])[CH2:19][CH2:18]1.Cl>C(O)C>[CH3:3][O:4][C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][C:14]=1[O:15][CH3:16])[N:11]=[CH:10][N:9]=[C:8]2[N:17]1[CH2:22][CH2:21][CH:20]([CH:23]([CH3:34])[CH2:24][N:25]2[CH2:30][CH2:29][CH:28]([CH3:31])[NH:27][S:26]2(=[O:32])=[O:33])[CH2:19][CH2:18]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 20434947HCID 20434947, compound

Product 1

HCID 20434941HCID 20434941, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Sodium borohydride (0.025 g) was added at room temperature to a stirred solution of 1-(6,7-dimethoxyquinazolin-4-yl)-4-[1-(1,1-dioxo-5-methyl-1,2,6-thiadiazin-2-yl)prop-2-yl]piperidine (0.30 g) (Example 35) in absolute ethanol (5 ml.). After stirring for 16 hours, the mixture was acidified to pH1 with 2M hydrochloric acid and concentrated in vacuo. The residue was treated with aqueous sodium carbonate solution to pH12, extracted with chloroform (3×10 ml.), and the combined extracts were dried (MgSO4) and evaporated to yield an oil which was chromatographed on silica ("Merck 60.9385") eluting with methanol:ethyl acetate, 1:20, to give a solid. Recrystallisation from ethyl acetate-ether afforded 1-(6,7-dimethoxyquinazolin-4-yl)-4-[1-(1,1-dioxo-5-methyltetrahydro-1,2,6-thiadiazin-2-yl)prop-2-yl]piperidine as white microcrystals, m.p. 172°-175°, (0.15 g).

Workup

  1. concentrationconcentrated in vacuo
  2. additionThe residue was treated with aqueous sodium carbonate solution to pH12
  3. extractionextracted with chloroform (3×10 ml.)
  4. dry with materialthe combined extracts were dried (MgSO4)
  5. customevaporated
  6. customto yield an oil which
  7. customwas chromatographed on silica ("Merck 60.9385")
  8. washeluting with methanol
  9. customethyl acetate, 1:20, to give a solid
  10. customRecrystallisation from ethyl acetate-ether

Sources & evidence

ORD record
ord-19c4a16921d8412994148d34cf9c321a
Source dataset
uspto-grants-1984_12
Patent number
US04489075

Reaction notes

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