Sodium borohydride → HCID 20266409, compound

HRID 1719704Notes

Reaction equation

HRID 1719704 reaction equation
[BH4-].[Na+].[O:3]=[C:4]([CH:15]1[CH2:20][CH2:19][N:18]([C:21]2[C:30]3[C:25](=[CH:26][C:27]([O:33][CH3:34])=[C:28]([O:31][CH3:32])[CH:29]=3)[N:24]=[CH:23][N:22]=2)[CH2:17][CH2:16]1)[CH2:5][N:6]1[CH:11]=[CH:10][C:9]([CH3:12])=[N:8][S:7]1(=[O:14])=[O:13]>C(O)C>[OH:3][CH:4]([CH:15]1[CH2:20][CH2:19][N:18]([C:21]2[C:30]3[C:25](=[CH:26][C:27]([O:33][CH3:34])=[C:28]([O:31][CH3:32])[CH:29]=3)[N:24]=[CH:23][N:22]=2)[CH2:17][CH2:16]1)[CH2:5][N:6]1[CH2:11][CH2:10][CH:9]([CH3:12])[NH:8][S:7]1(=[O:13])=[O:14]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 20266408HCID 20266408, compound

Product 1

HCID 20266409HCID 20266409, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Sodium borohydride (40 mg) was added at 0° to a stirred solution of 2-{2-oxo-2-[1-(6,7-dimethoxyquinazolin-4-yl)piperid-4-yl]ethyl}-5-methyl-1,2,6-thiadiazine-1,1-dioxide (0.4 g) in ethanol (10 cm3). After 2 hours the volatile material was removed in vacuo and the residue was partitioned between water (10 cm3) and dichloromethane (20 cm3). The dried organic extract was evaporated to give a solid which was chromatographed on silica ("Merck" 60.9385) eluting with methanol:chloroform, 1:19, to give a foam which was crystallised from ethyl acetate to afford 2-{2-hydroxy-2-[1-(6,7-dimethoxyquinazolin-4-yl)piperid-4-yl]ethyl}-5-methyltetrahydro-1,2,6-thiadiazine-1,1-dioxide as microcrystals, m.p. 189°-193° (0.30 g).

Workup

  1. customAfter 2 hours the volatile material was removed in vacuo
  2. customthe residue was partitioned between water (10 cm3) and dichloromethane (20 cm3)
  3. extractionThe dried organic extract
  4. customwas evaporated
  5. customto give a solid which
  6. customwas chromatographed on silica ("Merck" 60.9385)
  7. washeluting with methanol
  8. customchloroform, 1:19, to give a foam which
  9. customwas crystallised from ethyl acetate

Sources & evidence

ORD record
ord-25ba1cfb4dcd4dbd835938ce7afebb7a
Source dataset
uspto-grants-1985_09
Patent number
US04542132

Reaction notes

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