4-Bromobenzoyl chloride → HCID 67772177, compound

HRID 1808831Notes

Reaction equation

HRID 1808831 reaction equation
[CH2:1]([NH:3][C@@H:4]([CH:11]([CH3:13])[CH3:12])[CH2:5][N:6]1[CH2:10][CH2:9][CH2:8][CH2:7]1)[CH3:2].[Br:14][C:15]1[CH:23]=[CH:22][C:18]([C:19](Cl)=[O:20])=[CH:17][CH:16]=1>C(Cl)Cl>[Br:14][C:15]1[CH:23]=[CH:22][C:18]([C:19]([N:3]([CH2:1][CH3:2])[C@@H:4]([CH:11]([CH3:12])[CH3:13])[CH2:5][N:6]2[CH2:10][CH2:9][CH2:8][CH2:7]2)=[O:20])=[CH:17][CH:16]=1

Participants

4

Reactant 2

HCID 685154-Bromobenzoyl chlorideHCID 57266190HCID 57266190, compound

Product 1

HCID 67772177HCID 67772177, compoundYield 15%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (S)—N-ethyl-3-methyl-1-(pyrrolidin-1-yl)butan-2-amine (0.1 g, 0.54 mmol) (for synthesis, see e.g. EP254545) in DCM (2 mL) was TEA (0.075 mL, 0.54 mmol) and 4-bromobenzoyl chloride (0.119 g, 0.54 mmol) added. The resultant mixture was stirred at rt overnight. The mixture was washed with H2O (2 mL), filtered through a phase separator and concentrated under reduced pressure. The residue was purified by preparative HPLC to give the title compound (29 mg, 15%). Mixture of rotamers: 1H NMR (400 MHz, CD3OD) δ 0.77-1.13, 1.30, 1.66-2.06, 2.26-2.59, 2.62-2.91, 3.00-3.29, 3.43-3.69, 7.27-7.42, 7.52-7.70. Total no of protons: 27. HRMS (M+H)+: calculated 367.1385. found 367.1384.

Workup

  1. additionadded
  2. washThe mixture was washed with H2O (2 mL)
  3. filtrationfiltered through a phase separator
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-30144401a8cb4d61b264e3cc1c639c90
Source dataset
uspto-grants-2013_01
Patent number
US08361998B2

Reaction notes

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