N-bromobutanimide → HCID 22050291, compound

HRID 1867149Notes

Reaction equation

HRID 1867149 reaction equation
C1C(=O)N([Br:8])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:38]([O:40][CH3:41])=[O:39])[CH:11]=1>C(Cl)Cl>[Br:8][C:17]1[C:18](=[O:33])[N:19]([C:23]2[CH:24]=[C:25]([CH:29]=[CH:30][C:31]=2[CH3:32])[C:26]([OH:28])=[O:27])[C:20]([CH3:22])=[CH:21][C:16]=1[O:15][CH2:14][C:13]1[CH:34]=[CH:35][C:10]([F:9])=[CH:11][C:12]=1[CH2:36][NH:37][C:38]([O:40][CH3:41])=[O:39]

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 22050291HCID 22050291, 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%). 1H NMR (CD3OD/400 MHz) δ8.04 (m, 1H), 7.77 (s, 1H), 7.54 (m, 2H), 7.13 (m, 1H), 7.05 (m, 1H), 6.68 (s, 1H), 5.40 (s, 2H), 4.44 (s, 2H), 3.64 (s, 3H), 2.09 (s, 3H), 1.99 (s, 3H). ESHRMS m/z 533.0700 and 535.0677 (M+H calculated for C24H23BrFN2O6 requires 533.0718 and 535.0701).

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-bb3957fd1cc24ff5a875ffdf94d05577
Source dataset
uspto-grants-2009_12
Patent number
US07629363B2

Reaction notes

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