Sodium borohydride → HCID 69671881, compound

HRID 626812Notes

Reaction equation

HRID 626812 reaction equation
[Cl:1][C:2]1[C:3]([N:12]2[CH:29]=[C:15]3[C:16]([NH:21][C:22]4[CH:27]=[C:26]([CH3:28])[N:25]=[CH:24][N:23]=4)=[N:17][CH:18]=[C:19]([F:20])[C:14]3=[N:13]2)=[C:4]([CH:7]=[C:8]([CH:10]=[O:11])[CH:9]=1)[C:5]#[N:6].[BH4-].[Na+]>C(O)C.C1COCC1>[Cl:1][C:2]1[C:3]([N:12]2[CH:29]=[C:15]3[C:16]([NH:21][C:22]4[CH:27]=[C:26]([CH3:28])[N:25]=[CH:24][N:23]=4)=[N:17][CH:18]=[C:19]([F:20])[C:14]3=[N:13]2)=[C:4]([CH:7]=[C:8]([CH2:10][OH:11])[CH:9]=1)[C:5]#[N:6]

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 86697085HCID 86697085, compound

Product 1

HCID 69671881HCID 69671881, compoundYield 16.3%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-chloro-2-[7-fluoro-4-(6-methylpyrimidin-4-ylamino)pyrazolo[4,3-c]pyridin-2-yl]-5-formylbenzonitrile (24 mg, 0.06 mmol) in ethanol (IMS grade, 2.0 mL) and THF (2.0 mL) was added sodium borohydride (4 mg, 0.1 mmol) and the reaction mixture was stirred at room temperature for 2 hours. The resultant mixture was partitioned between ethyl acetate and water and the layers were separated. The organic layer was washed with brine, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The residue was triturated with diethyl ether and the solid obtained was filtered and dried. This was then purified by silica gel flash chromatography (0-1% methanol in ethyl acetate) to afford the title compound as a white solid (4.0 mg, 16% yield). 1H NMR (400 MHz, DMSO-d6): δ 10.82 (s, 1H), 9.46 (d, J=2.6 Hz, 1H), 8.71 (d, J=1.2 Hz, 1H), 8.38 (s, 1H), 8.09 (m, 2H), 8.03 (d, J=3.5 Hz, 1H), 5.76 (t, J=5.8 Hz, 1H), 4.71 (d, J=5.8 Hz, 2H), 2.46 (s, 3H). LCMS (Method B): RT=2.78 min, m/z: 410 [M+H+].

Workup

  1. customThe resultant mixture was partitioned between ethyl acetate and water
  2. customthe layers were separated
  3. washThe organic layer was washed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was triturated with diethyl ether
  8. customthe solid obtained
  9. filtrationwas filtered
  10. customdried
  11. customThis was then purified by silica gel flash chromatography (0-1% methanol in ethyl acetate)

Sources & evidence

ORD record
ord-95cb4cdb7bd94f1f88bd6ba1a3374614
Source dataset
uspto-grants-2016_04
Patent number
US09309240B2

Reaction notes

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