Sodium borohydride → HCID 71115014, compound

HRID 468875Notes

Reaction equation

HRID 468875 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:30])=[C:6]([C:8]2[CH:17]=[C:16]3[C:11]([CH:12]=[C:13]([NH:18][C:19]([CH:21]4[CH2:23][CH2:22]4)=[O:20])[N:14]=[CH:15]3)=[C:10]([CH:24]3[CH2:28][CH:27]([OH:29])[O:26][CH2:25]3)[N:9]=2)[CH:7]=1.[BH4-].[Na+]>O1CCCC1.C(OCC)(=O)C>[OH:26][CH2:25][CH:24]([C:10]1[N:9]=[C:8]([C:6]2[CH:7]=[C:2]([F:1])[CH:3]=[CH:4][C:5]=2[CH3:30])[CH:17]=[C:16]2[C:11]=1[CH:12]=[C:13]([NH:18][C:19]([CH:21]1[CH2:23][CH2:22]1)=[O:20])[N:14]=[CH:15]2)[CH2:28][CH2:27][OH:29]

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 71115175HCID 71115175, compound

Product 1

HCID 71115014HCID 71115014, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of N-(7-(5-fluoro-2-methylphenyl)-5-(5-hydroxytetrahydrofuran-3-yl)-2,6-naphthyridin-3-yl)cyclopropanecarboxamide (45 mg, 0.11 mmol) in tetrahydrofuran (1 mL) cooled at 0° C. was added sodium tetrahydroborate (8.4 mg, 0.22 mmol), and the reaction mixture was stirred at this temperature for 1 hour. The reaction mixture was diluted with ethyl acetate (50 mL) and washed with water (100 mL). The organic layer was separated, dried over sodium sulfate, filtered, and evaporated in vacuo to afford a residue that was used in the next step without further purification.

Workup

  1. washwashed with water (100 mL)
  2. customThe organic layer was separated
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. customevaporated in vacuo
  6. customto afford a residue that
  7. customwas used in the next step without further purification

Sources & evidence

ORD record
ord-069b5cafb9a741a4b6d794423254e020
Source dataset
uspto-grants-2014_01
Patent number
US08623889B2

Reaction notes

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