Water → HCID 66821897, compound

HRID 1894672Notes

Reaction equation

HRID 1894672 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[C:9]([NH:12][CH2:13][CH2:14][O:15][CH3:16])[C:8]([C@@H:17]([NH:19][C:20]1[N:25]3[N:26]=[CH:27][CH:28]=[C:24]3[N:23]=[C:22](S(C)(=O)=O)[N:21]=1)[CH3:18])=[CH:7]2.[BH4-].[Na+].O>CCO.C(Cl)(Cl)Cl>[Cl:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[C:9]([NH:12][CH2:13][CH2:14][O:15][CH3:16])[C:8]([C@@H:17]([NH:19][C:20]1[N:25]3[N:26]=[CH:27][CH:28]=[C:24]3[N:23]=[CH:22][N:21]=1)[CH3:18])=[CH:7]2

Participants

5

Reactant 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 46871372HCID 46871372, compound

Product 1

HCID 66821897HCID 66821897, compoundYield 62.8%

Reagents, catalysts & solvents 1

HCID 21889567Chloroform ethanolSolvent

Procedure

To a solution of Example 20 (60 mg, 0.12 mmol) in EtOH/CHCl3 (1:1; 1.2 mL) was added portionwise NaBH4 (9.6 mg, 0.25 mmol). After 10 minutes of stirring, water (1 mL) was added and the reaction mixture was concentrated in vacuo. The residue was partitioned between DCM and water. The organic layer was washed with water (2×10 mL) and brine (10 mL), dried (MgSO4) and concentrated in vacuo. The resulting gum was freeze-dried to give the title compound (30 mg, 60%) as an off-white solid. δH (CDCl3) 8.28 (1H, s), 7.96 (1H, d, J=2.14 Hz), 7.90 (1H, s), 7.65 (1H, dd, J 7.56, 1.39 Hz), 7.52 (1H, dd, J 7.97, 1.41 Hz), 7.12 (1H, t, J=7.76 Hz), 6.59 (1H, br d, J=9.42 Hz), 6.48-6.46 (2H, m), 5.75-5.66 (1H, m), 3.94-3.85 (1H, m), 3.83-3.74 (1H, m), 3.65-3.51 (2H, m), 3.18 (3H, s), 1.86 (3H, d, J=6.80 Hz). LCMS (ES+) 398 (M+H)+, RT 19.67 minutes (Method 6).

Workup

  1. concentrationthe reaction mixture was concentrated in vacuo
  2. customThe residue was partitioned between DCM and water
  3. washThe organic layer was washed with water (2×10 mL) and brine (10 mL)
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated in vacuo
  6. customThe resulting gum was freeze-dried

Sources & evidence

ORD record
ord-827a743c31f04058b8781d0f366856a7
Source dataset
uspto-grants-2013_08
Patent number
US08513284B2

Reaction notes

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