N-bromobutanimide → HCID 22050793, compound

HRID 1832104Notes

Reaction equation

HRID 1832104 reaction equation
[CH2:1]1C(=O)N(Br)C(=O)C1.[F:9][C:10]1[CH:35]=[CH:34][C:13]([CH2:14][O:15][C:16]2[CH:21]=[C:20]([CH3:22])[N:19]([C:23]3[CH:24]=[C:25]([CH:29]=[CH:30][C:31]=3[CH3:32])[C:26]([OH:28])=[O:27])[C:18](=[O:33])[CH:17]=2)=[C:12]([CH2:36][NH:37]C(OC)=O)[CH:11]=1>C(Cl)Cl>[C:36]([C:12]1[CH:11]=[C:10]([F:9])[CH:35]=[CH:34][C:13]=1[CH2:14][O:15][C:16]1[CH:21]=[C:20]([CH3:22])[N:19]([C:23]2[CH:24]=[C:25]([CH:29]=[CH:30][C:31]=2[CH3:32])[C:26]([O:28][CH3:1])=[O:27])[C:18](=[O:33])[CH:17]=1)#[N:37]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 220506313-[4-[(4-fluoro-2-{[(methoxycarbonyl)amino]methyl}benzyl)oxy]-6-methyl-2-oxopyridin-1(2H)-yl]-4-methylbenzoic Acid

Product 1

HCID 22050793HCID 22050793, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

NBS (0.69 g, 3.85 mmol) was added to a solution of 3-[4-[(4-fluoro-2-{[(methoxycarbonyl)amino]methyl}benzyl)oxy]-6-methyl-2-oxopyridin-1(2H)-yl]-4-methylbenzoic acid (from Step 4) (1.75 g, 3.85 mmol) in DCM (45 mL). After 1.5 h, solvent removed on rotary evaporator. Solid dissolved in EtOAc and hexane added, resulting in a solid precipitate. Solid filtered. Solid subsequently dissolved in DCM and washed with water. Organic layer dried over Na2SO4, filtered, and concentrated. Pale yellow solid dried in vacuo (1.47 g, 72%).

Workup

  1. customsolvent removed on rotary evaporator
  2. dissolutionSolid dissolved in EtOAc
  3. additionhexane added
  4. customresulting in a solid precipitate
  5. filtrationSolid filtered
  6. dissolutionSolid subsequently dissolved in DCM
  7. washwashed with water
  8. dry with materialOrganic layer dried over Na2SO4
  9. filtrationfiltered
  10. concentrationconcentrated
  11. customPale yellow solid dried in vacuo (1.47 g, 72%)

Sources & evidence

ORD record
ord-1c302f0e1652435faecd8c25f3584d25
Source dataset
uspto-grants-2006_06
Patent number
US07067540B2

Reaction notes

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