N-bromobutanimide → HCID 57826575, compound

HRID 2391989Notes

Reaction equation

HRID 2391989 reaction equation
[Cl:1][C:2]1[S:6][C:5]([C:7]([NH:9][C@@H:10]([CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=2[C:27]([F:30])([F:29])[F:28])[CH2:11][NH:12][C:13](=[O:19])[O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:8])=[CH:4][C:3]=1[C:31]1[N:35]([CH3:36])[N:34]=[CH:33][CH:32]=1.[Br:37]N1C(=O)CCC1=O>C1COCC1>[Br:37][C:32]1[CH:33]=[N:34][N:35]([CH3:36])[C:31]=1[C:3]1[CH:4]=[C:5]([C:7]([NH:9][C@@H:10]([CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=2[C:27]([F:30])([F:28])[F:29])[CH2:11][NH:12][C:13](=[O:19])[O:14][C:15]([CH3:16])([CH3:18])[CH3:17])=[O:8])[S:6][C:2]=1[Cl:1]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 57826434HCID 57826434, compound

Product 1

HCID 57826575HCID 57826575, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 1,1-dimethylethyl {(2S)-2-({[5-chloro-4-(1-methyl-1H-pyrazol-5-yl)-2-thienyl]carbonyl}amino)-3-[2-(trifluoromethyl)phenyl]propyl}carbamate (121 mg, 0.22 mmol)[prepared in Example 25] and N-bromosuccinimide (52 mg, 0.290 mmol) in THF (2 mL) was stirred in a sealed tube at 70° C. After 1 h, the solution was partitioned between H2O-DCM and the aqueous phase was washed several times with DCM. The combined organic fractions were dried (Na2SO4), concentrated under vacuum and used directly without further purification: LCMS (ES) m/z=622 (M+H)+.

Workup

  1. customthe solution was partitioned between H2O-DCM
  2. washthe aqueous phase was washed several times with DCM
  3. dry with materialThe combined organic fractions were dried (Na2SO4)
  4. concentrationconcentrated under vacuum
  5. customused directly without further purification

Sources & evidence

ORD record
ord-45fa3dcc47a94542a3e2a1073cee86fa
Source dataset
uspto-grants-2012_09
Patent number
US08273782B2

Reaction notes

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