Acetic Acid → HCID 59525902, compound

HRID 385832Notes

Reaction equation

HRID 385832 reaction equation
[Br:1][C:2]1[N:7]=[C:6]([CH2:8][NH:9][CH2:10][C:11]([NH:13][CH:14]2[CH2:18][CH2:17][CH2:16][CH2:15]2)=[O:12])[CH:5]=[CH:4][CH:3]=1.C=O.[C:21](O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCl>[Br:1][C:2]1[N:7]=[C:6]([CH2:8][N:9]([CH3:21])[CH2:10][C:11]([NH:13][CH:14]2[CH2:18][CH2:17][CH2:16][CH2:15]2)=[O:12])[CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 712FormaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 59526375HCID 59526375, compound

Product 1

HCID 59525902HCID 59525902, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

N2-[(6-Bromopyridin-2-yl)methyl]-N-cyclopentylglycinamide (Example 187, Step 1) (0.33 g, 1.06 mmol) was dissolved in dichloromethane (5.30 mL) and formaldehyde (0.087 mL, 1.17 mmol) and acetic acid (0.12 mL, 2.12 mmol) were added. The reaction was stirred for 45 minutes and sodium triacetoxyborohydride (0.36 g, 1.70 mmol) was added. Once complete, the reaction was then quenched with water and extracted with ethyl acetate. The organic layer was dried over magnesium sulfate, filtered and concentrated. The crude mixture was purified by silica gel chromatography to yield the title compound.

Workup

  1. customOnce complete, the reaction was then quenched with water
  2. extractionextracted with ethyl acetate
  3. dry with materialThe organic layer was dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude mixture was purified by silica gel chromatography

Sources & evidence

ORD record
ord-a87b1507555c43a2812d28a5ffa0e44a
Source dataset
uspto-grants-2013_02
Patent number
US08367706B2

Reaction notes

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