Water → 1-{12-Methyl-4-[3-methyl-1-(propan-2-yl)-1H-1,2,4-triazol-5-yl]-9-oxa-3,6-diazatricyclo[8.4.0.02,6]tetradeca-1(14),2,4,10,12-pentaen-13-yl}ethan-1-ol

HRID 1530707Notes

Reaction equation

HRID 1530707 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]2[C:13](=[CH:14][C:15]=1[C:16](=[O:18])[CH3:17])[C:12]1[N:8]([CH:9]=[C:10]([C:19]3[N:23]([CH:24]([CH3:26])[CH3:25])[N:22]=[C:21]([CH3:27])[N:20]=3)[N:11]=1)[CH2:7][CH2:6][O:5]2.[BH4-].[Na+].O>CO>[CH3:1][C:2]1[CH:3]=[C:4]2[C:13](=[CH:14][C:15]=1[CH:16]([OH:18])[CH3:17])[C:12]1[N:8]([CH:9]=[C:10]([C:19]3[N:23]([CH:24]([CH3:26])[CH3:25])[N:22]=[C:21]([CH3:27])[N:20]=3)[N:11]=1)[CH2:7][CH2:6][O:5]2

Participants

5

Reactant 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 683128931-{12-Methyl-4-[3-methyl-1-(propan-2-yl)-1H-1,2,4-triazol-5-yl]-9-oxa-3,6-diazatricyclo[8.4.0.02,6]tetradeca-1(14),2,4,10,12-pentaen-13-yl}ethan-1-one

Product 1

HCID 683127771-{12-Methyl-4-[3-methyl-1-(propan-2-yl)-1H-1,2,4-triazol-5-yl]-9-oxa-3,6-diazatricyclo[8.4.0.02,6]tetradeca-1(14),2,4,10,12-pentaen-13-yl}ethan-1-olYield 58%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 1-{12-methyl-4-[3-methyl-1-(propan-2-yl)-1H-1,2,4-triazol-5-yl]-9-oxa-3,6-diazatricyclo[8.4.0.02,6]tetradeca-1(14),2,4,10,12-pentaen-13-yl}ethan-1-one (2.20 g) in MeOH (50.0 mL) was added NaBH4 (920 mg, 24.2 mmol). The mixture was stirred at room temperature for 2 hrs. Water was added to quench the reaction. The mixture was extracted with ethyl acetate (5×50 mL). The combined organic layers were washed with brine and dried over MgSO4. Removal of the solvent gave the crude product, which was purified by reverse phase Combi-flash eluting with a 25-30% gradient of CH3CN in 0.3% NH4HCO3 to afford the racemic product (800 mg, 58% yield for three steps). 1H NMR (500 MHz, DMSO-d6) δ 8.50 (s, 1H), 7.85 (s, 1H), 6.81 (s, 1H), 5.74 (m, 1H), 5.07 (s, 1H), 4.87 (s, 1H), 4.48-4.44 (m, 4H), 2.28 (s, 3H), 2.25 (s, 3H), 1.46 (s, 6H), 1.33 (s, 3H). LCMS m/z [M+H]+ 368.2

Workup

  1. customto quench
  2. customthe reaction
  3. extractionThe mixture was extracted with ethyl acetate (5×50 mL)
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over MgSO4
  6. customRemoval of the solvent

Sources & evidence

ORD record
ord-1c77bcd917924969ba6af245062ab99f
Source dataset
uspto-grants-2015_07
Patent number
US09090628B2

Reaction notes

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