2-Butanone, 3-bromo- → HCID 54675680, compound

HRID 2203359Notes

Reaction equation

HRID 2203359 reaction equation
[NH2:1][C:2]1[C:3]2[C:29]([CH3:33])([C:30](=[S:32])[NH2:31])[C:28](=[O:34])[NH:27][C:4]=2[N:5]=[C:6]([C:8]2[C:16]3[C:11](=[CH:12][C:13]([Cl:17])=[CH:14][CH:15]=3)[N:10]([CH2:18][CH2:19][C:20]([F:26])([F:25])[C:21]([F:24])([F:23])[F:22])[N:9]=2)[N:7]=1.Br[CH:36]([CH3:40])[C:37](=O)[CH3:38]>C(O)C>[NH2:1][C:2]1[C:3]2[C:29]([C:30]3[S:32][C:36]([CH3:40])=[C:37]([CH3:38])[N:31]=3)([CH3:33])[C:28](=[O:34])[NH:27][C:4]=2[N:5]=[C:6]([C:8]2[C:16]3[C:11](=[CH:12][C:13]([Cl:17])=[CH:14][CH:15]=3)[N:10]([CH2:18][CH2:19][C:20]([F:26])([F:25])[C:21]([F:24])([F:22])[F:23])[N:9]=2)[N:7]=1

Participants

4

Reactant 2

HCID 131422-Butanone, 3-bromo-HCID 86678994HCID 86678994, compound

Product 1

HCID 54675680HCID 54675680, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of the intermediate from Step A above (11 mg, 0.021 mmol) in ethanol (423 μl), was added 3-bromo-2-butanone (32.0 mg, 0.212 mmol). The mixture was stirred at 80° C. overnight. The solvent was then removed in vacuo. The residue was purified by preparative TLC using hexanes/EtOAc (1/1) as the eluent to give the indicated compound. Chiral separation using SFC on a Chiralpak AD column provided both enantiomers of the title compound. 1H NMR (500 MHz, CH3OH-d4): δ 8.59 (d, J=8.7 Hz, 1H); 7.86 (s, 1H); 7.36 (d, J=8.7 Hz, 1H); 4.92-4.82 (m, 2H); 3.08-2.88 (m, 2H); 2.38 (s, 3H); 2.34 (s, 3H); 1.94 (s, 3H). m/z=572.0 (M+H).

Workup

  1. customThe solvent was then removed in vacuo
  2. customThe residue was purified by preparative TLC
  3. customto give the indicated compound
  4. customChiral separation

Sources & evidence

ORD record
ord-3e397aa917cf493fbb1d26c60825c258
Source dataset
uspto-grants-2016_06
Patent number
US09365574B2

Reaction notes

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