Water → HCID 118509542, compound

HRID 1487279Notes

Reaction equation

HRID 1487279 reaction equation
[Br:1][C:2]1[CH:11]=[CH:10][C:9]([F:12])=[CH:8][C:3]=1[NH:4][CH:5]([CH3:7])[CH3:6].CCN(C(C)C)C(C)C.[CH:22]1([C:25](Cl)=[O:26])[CH2:24][CH2:23]1.O>C(Cl)Cl>[Br:1][C:2]1[CH:11]=[CH:10][C:9]([F:12])=[CH:8][C:3]=1[N:4]([CH:5]([CH3:7])[CH3:6])[C:25]([CH:22]1[CH2:24][CH2:23]1)=[O:26]

Participants

6

Reactant 4

HCID 962WaterHCID 77637Cyclopropanecarbonyl chlorideHCID 81531DiisopropylethylamineHCID 103750657HCID 103750657, compound

Product 1

HCID 118509542HCID 118509542, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
20 °C

Procedure

2-Bromo-5-fluoro-N-(propan-2-yl)aniline E-1.7′″″ (2.20 g; 9.48 mmol) is suspended in 5 ml DCM and DIPEA (8.2 ml; 47.40 mmol) is added. Afterwards cyclopropanecarbonyl chloride (3.44 ml; 75.84 mmol) is added and the reaction mixture is stirred for 24 h at 20° C. The reaction mixture is poured into water and extracted with DCM. The combined organic layer is dried over MgSO4 and concentrated under reduced pressure. The crude product is purified using reversed phase chromatography (Method: prep. HPLC1).

Workup

  1. extractionextracted with DCM
  2. dry with materialThe combined organic layer is dried over MgSO4
  3. concentrationconcentrated under reduced pressure
  4. customThe crude product is purified

Sources & evidence

ORD record
ord-da17f3bc4fb04a6f9140207bcacfea61
Source dataset
uspto-grants-2016_08
Patent number
US09428515B2

Reaction notes

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