N-bromobutanimide → HCID 118045459, compound

HRID 595937Notes

Reaction equation

HRID 595937 reaction equation
[NH2:1][C:2]1[C:3]([C:8]2[CH:26]=[CH:25][C:11]([C:12]([NH:14][C@@H:15]([C:18]3[CH:23]=[CH:22][CH:21]=[C:20]([Cl:24])[CH:19]=3)[CH2:16][OH:17])=[O:13])=[C:10]([F:27])[CH:9]=2)=[N:4][CH:5]=[CH:6][N:7]=1.C1C(=O)N([Br:35])C(=O)C1>C(#N)C>[NH2:1][C:2]1[C:3]([C:8]2[CH:26]=[CH:25][C:11]([C:12]([NH:14][C@@H:15]([C:18]3[CH:23]=[CH:22][CH:21]=[C:20]([Cl:24])[CH:19]=3)[CH2:16][OH:17])=[O:13])=[C:10]([F:27])[CH:9]=2)=[N:4][C:5]([Br:35])=[CH:6][N:7]=1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 118046006(S)-4-(3-aminopyrazin-2-yl)-N-(1-(3-chlorophenyl)-2-hydroxyethyl)-2-fluorobenzamide

Product 1

HCID 118045459HCID 118045459, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of (S)-4-(3-aminopyrazin-2-yl)-N-(1-(3-chlorophenyl)-2-hydroxyethyl)-2-fluorobenzamide (389 mg, 1.006 mmol) in acetonitrile (21 mL) was added NBS (171 mg, 0.961 mmol) at 0° C. The reaction mixture was stirred at 0° C. for 20 min. After quenched with sat NaHCO3, and stir for 30 min. The reaction mixture was extracted with EtOAc 3 times, the organic was washed by sat NaHCO3, water and brine, dried, filtered off, and concentrated. The crude material was taken to the next step without further purification. LCMS (m/z): 367 (MH+), 0.88 min.

Workup

  1. customAfter quenched with sat NaHCO3
  2. stirringstir for 30 min
  3. extractionThe reaction mixture was extracted with EtOAc 3 times
  4. washthe organic was washed
  5. customdried
  6. filtrationfiltered off
  7. concentrationconcentrated
  8. customThe crude material was taken to the next step without further purification
  9. custom367 (MH+), 0.88 min.

Sources & evidence

ORD record
ord-47e21b25db9644ac9233e455464624da
Source dataset
uspto-grants-2016_01
Patent number
US09242996B2

Reaction notes

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