N-bromobutanimide → HCID 57826575, compound

HRID 1845394Notes

Reaction equation

HRID 1845394 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-0883eae7a72645329e6de944441268fc
Source dataset
uspto-grants-2015_02
Patent number
US08946278B2

Reaction notes

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