Isobutyryl chloride → HCID 67345755, compound

HRID 1670000Notes

Reaction equation

HRID 1670000 reaction equation
[CH2:1]([N:8]1[CH2:12][CH2:11][C@H:10]([NH:13][C:14]2[CH:19]=[CH:18][C:17]([F:20])=[CH:16][C:15]=2[F:21])[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:22](Cl)(=[O:26])[CH:23]([CH3:25])[CH3:24]>CN(C1C=CN=CC=1)C.N1C=CC=CC=1>[CH2:1]([N:8]1[CH2:12][CH2:11][C@H:10]([N:13]([C:22](=[O:26])[CH:23]([CH3:25])[CH3:24])[C:14]2[CH:19]=[CH:18][C:17]([F:20])=[CH:16][C:15]=2[F:21])[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 62325Isobutyryl chlorideHCID 29080954HCID 29080954, compound

Product 1

HCID 67345755HCID 67345755, compoundYield 86%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1049PyridineSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of (3S)-1-benzyl-3-[(2,4-difluorophenyl)amino]pyrrolidine (150 mg, 0.52 mmol) and DMAP (6 mg, 0.05 mmol) in pyridine (7 mL) was added isobutyryl chloride (0.16 mL, 1.5 mmol) at 0° C. After being stirred at 60° C. for 18 h, the reaction mixture was quenched with an aqueous NaH(CO)3 solution and extracted with EtOAc. The extracts were concentrated in vacuo, the reside was purified by column chomatography (MeOH/CHCl3=1/25) to give the title compound (160 mg, 86.0%).

Workup

  1. customthe reaction mixture was quenched with an aqueous NaH(CO)3 solution
  2. extractionextracted with EtOAc
  3. concentrationThe extracts were concentrated in vacuo
  4. customthe reside was purified by column chomatography (MeOH/CHCl3=1/25)

Sources & evidence

ORD record
ord-18bff5a31abe45a7ba74c1cfd5a5ef9e
Source dataset
uspto-grants-2011_08
Patent number
US07989634B2

Reaction notes

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