Diisopropylethylamine → HCID 67774546, compound

HRID 1808816Notes

Reaction equation

HRID 1808816 reaction equation
[CH3:1][O:2][C@H:3]([CH3:13])[C@H:4]([NH:11][CH3:12])[CH2:5][N:6]1[CH2:10][CH2:9][CH2:8][CH2:7]1.CCN(C(C)C)C(C)C.[F:23][C:24]1[CH:32]=[CH:31][C:27]([C:28](Cl)=[O:29])=[CH:26][C:25]=1[CH3:33]>C(Cl)Cl>[F:23][C:24]1[CH:32]=[CH:31][C:27]([C:28]([N:11]([C@@H:4]([C@H:3]([O:2][CH3:1])[CH3:13])[CH2:5][N:6]2[CH2:10][CH2:9][CH2:8][CH2:7]2)[CH3:12])=[O:29])=[CH:26][C:25]=1[CH3:33]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 27745894-Fluoro-3-methylbenzoyl chlorideHCID 67773810HCID 67773810, compound

Product 1

HCID 67774546HCID 67774546, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of (2R,3R)-3-methoxy-N-methyl-1-(pyrrolidin-1-yl)butan-2-amine (Compound M6) (80 mg, 0.43 mmol) in DCM (1.5 mL) was DIPEA (0.090 mL, 0.52 mmol) and 4-fluoro-3-methylbenzoyl chloride (0.061 mL, 0.43 mmol) added. The resultant mixture was stirred at rt overnight. The mixture was diluted with DCM (5 mL), washed with NaHCO3 (saturated, 5 mL), filtered through a phase separator and concentrated under reduced pressure. The residue was purified by preparative HPLC to give the title compound (102 mg, 74%).

Workup

  1. additionadded
  2. washwashed with NaHCO3 (saturated, 5 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-21e87bbe5a6a490f94cfcdc1337df0db
Source dataset
uspto-grants-2013_01
Patent number
US08361998B2

Reaction notes

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