Triethylamine → HCID 118223449, compound

HRID 2200109Notes

Reaction equation

HRID 2200109 reaction equation
[CH3:1][C:2]1([C:5](Cl)=[O:6])[CH2:4][CH2:3]1.[F:8][C:9]1[CH:22]=[C:21]([N+:23]([O-:25])=[O:24])[CH:20]=[CH:19][C:10]=1[O:11][C:12]1[CH:17]=[CH:16][N:15]=[C:14]([NH2:18])[CH:13]=1.CCN(CC)CC.CCOC(C)=O>C(Cl)Cl>[F:8][C:9]1[CH:22]=[C:21]([N+:23]([O-:25])=[O:24])[CH:20]=[CH:19][C:10]=1[O:11][C:12]1[CH:17]=[CH:16][N:15]=[C:14]([NH:18][C:5]([C:2]2([CH3:1])[CH2:4][CH2:3]2)=[O:6])[CH:13]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 127899391-Methylcyclopropane-1-carbonyl chlorideHCID 231531982-Amino-4-(2-fluoro-4-nitrophenoxy)pyridine

Product 1

HCID 118223449HCID 118223449, compoundYield 24%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Add the solution of the above 1-methylcyclopropanecarbonyl chloride in DCM slowly to a solution of 4-(2-fluoro-4-nitro-phenoxy)pyridin-2-amine (500 mg, 2.0 mmol) and Et3N (505 mg, 5.0 mmol) in DCM (15 mL) at 0° C. Stir the reaction at room temperature for 15 hrs. TLC (EtOAc:PE=1:1) shows the reaction is complete. Concentrate the mixture to give the crude product. Purification by chromatography (silica gel, EtOAc:PE=1:1) affords the target compound (160 mg, 24%). MS: (M+1): 332.2.

Workup

  1. customthe reaction at room temperature for 15 hrs
  2. concentrationConcentrate the mixture
  3. customto give the crude product
  4. customPurification by chromatography (silica gel, EtOAc:PE=1:1)

Sources & evidence

ORD record
ord-a69d4a5d81f84ea8b56f7127211c1ab4
Source dataset
uspto-grants-2016_06
Patent number
US09359338B2

Reaction notes

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