Sodium borohydride → HCID 90386113, compound

HRID 2170166Notes

Reaction equation

HRID 2170166 reaction equation
[CH2:1]([NH:8][C:9]1[C:14]2=[C:15]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[CH:16]=[CH:17][N:13]2[N:12]=[C:11]([C:24]2[CH:25]=[N:26][CH:27]=[C:28]([CH:31]=2)[CH:29]=[O:30])[N:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[BH4-].[Na+]>CO.O>[CH2:1]([NH:8][C:9]1[C:14]2=[C:15]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[CH:16]=[CH:17][N:13]2[N:12]=[C:11]([C:24]2[CH:31]=[C:28]([CH2:29][OH:30])[CH:27]=[N:26][CH:25]=2)[N:10]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 78324582HCID 78324582, compound

Product 1

HCID 90386113HCID 90386113, compoundYield 50%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a solution of 5-(4-(benzylamino)-5-phenylpyrrolo[2,1-f][1,2,4]triazin-2-yl)nicotinaldehyde (30.0 mg, 0.0740 mmol) in methanol (25 mL) was added NaBH4 (8.40 mg, 0.220 mmol). Reaction mixture was stirred at room temperature for 3 h and diluted with cold water (50 mL). The aqueous solution was extracted with ethyl acetate (2×50 mL). The combined organic layer was washed with saturated brain solution, dried over anhydrous sodium sulfate, filtered and evaporated under reduced pressure to give a residue which was purified by column chromatography using CombiFlash (REDISEP®, silica gel, 12 g, 40% EtOAc/hexanes) to get (5-(4-(benzylamino)-5-phenylpyrrolo[2,1-f][1,2,4]triazin-2-yl)pyridin-3-yl)methanol (15.0 mg, 50.0%). LCMS Condition B-12: retention time 2.15 min, [M+1]=406.2. HPLC Condition B-2: retention time 9.20 min, Purity 98.03%. 1H NMR (400 MHz, DMSO-d6) δ ppm 4.64 (d, J=5.7 Hz, 2H), 4.82 (d, J=5.7 Hz, 2H), 5.45 (t, J=5.7 Hz, 1H), 6.64 (t, J=5.2 Hz, 1H), 6.80 (d, J=2.7 Hz, 1H), 7.22-7.55 (m, 10H), 7.90 (d, J=2.7 Hz, 1H), 8.49 (t, J=2.1 Hz, 1H), 8.59 (d, J=2.0 Hz, 1H), 9.24 (d, J=2.0 Hz, 1H).

Workup

  1. customReaction mixture
  2. extractionThe aqueous solution was extracted with ethyl acetate (2×50 mL)
  3. washThe combined organic layer was washed with saturated brain solution
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. customevaporated under reduced pressure
  7. customto give a residue which
  8. customwas purified by column chromatography

Sources & evidence

ORD record
ord-41dddd2d773e43f4b23582ca181c0c10
Source dataset
uspto-grants-2015_06
Patent number
US09050345B2

Reaction notes

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