Sodium borohydride → HCID 86684609, compound

HRID 1022254Notes

Reaction equation

HRID 1022254 reaction equation
[CH3:1][O:2][CH2:3][C:4]1[N:8]([CH3:9])[N:7]=[C:6]([NH:10][C:11]2[C:16](=[O:17])[N:15]([CH3:18])[CH:14]=[C:13]([C:19]3[C:24]([CH:25]=[O:26])=[C:23]([N:27]4[CH2:39][CH2:38][C:37]5[N:36]6[C:31]([CH2:32][CH2:33][CH2:34][CH2:35]6)=[CH:30][C:29]=5[C:28]4=[O:40])[N:22]=[CH:21][CH:20]=3)[CH:12]=2)[CH:5]=1.[BH4-].[Na+]>CO>[OH:26][CH2:25][C:24]1[C:23]([N:27]2[CH2:39][CH2:38][C:37]3[N:36]4[C:31]([CH2:32][CH2:33][CH2:34][CH2:35]4)=[CH:30][C:29]=3[C:28]2=[O:40])=[N:22][CH:21]=[CH:20][C:19]=1[C:13]1[CH:12]=[C:11]([NH:10][C:6]2[CH:5]=[C:4]([CH2:3][O:2][CH3:1])[N:8]([CH3:9])[N:7]=2)[C:16](=[O:17])[N:15]([CH3:18])[CH:14]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 86684608HCID 86684608, compound

Product 1

HCID 86684609HCID 86684609, compoundYield 41.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 336e (100 mg, 0.18 mmol) in methanol (10 mL) was added NaBH4 (41 mg, 1.08 mmol). The mixture was stirred at room temperature for 1 h and LCMS showed the starting material had disappeared. The reaction was quenched with 1.0 M HCl solution (10 mL) and evaporated under reduced pressure until most of methanol was distilled. The residue was extracted with dichloromethane (3×15 mL). The combined organic layer was dried with Na2SO4 and evaporated under reduced pressure. The residue was purified by reverse-phase prep-HPLC to afford 336 as a white solid (41 mg, 41%). MS-ESI: [M+H]+ 544.2. 1H NMR (500 MHz, CDCl3) δ 8.49 (d, J=5.0 Hz, 1H), 7.96 (d, J=2.5 Hz, 1H), 7.73 (d, J=2.5 Hz, 1H), 7.41 (s, 1H), 7.33 (d, J=5.0 Hz, 1H), 6.33 (s, 1H), 5.95 (s, 1H), 4.99-4.96 (m, 1H), 4.67-4.64 (m, 1H), 4.42-4.41 (m, 3H), 4.36-4.26 (m, 1H), 3.98-3.91 (m, 1H), 3.88-3.82 (m, 2H), 3.79 (s, 3H), 3.71 (s, 3H), 3.37 (s, 3H), 3.06-2.91 (m, 2H), 2.87-2.79 (m, 2H), 2.08-2.01 (m, 2H), 1.91-1.86 (m, 2H).

Workup

  1. customThe reaction was quenched with 1.0 M HCl solution (10 mL)
  2. customevaporated under reduced pressure until most of methanol
  3. distillationwas distilled
  4. extractionThe residue was extracted with dichloromethane (3×15 mL)
  5. dry with materialThe combined organic layer was dried with Na2SO4
  6. customevaporated under reduced pressure
  7. customThe residue was purified by reverse-phase prep-HPLC

Sources & evidence

ORD record
ord-6b06044e0542460c895fbb08debc7241
Source dataset
uspto-grants-2014_05
Patent number
US08716274B2

Reaction notes

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