Ethyl Acetate → HCID 118223407, compound

HRID 2200180Notes

Reaction equation

HRID 2200180 reaction equation
Cl[C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:17])OC2C=CC=CC=2)=[CH:4][C:3]=1[C:18]([F:21])([F:20])[F:19].[CH:22]1[CH:23]=[CH:24][C:25]2N(O)N=[N:28][C:26]=2C=1.F[C:33](F)(F)[C:34]1[CH:35]=C(N)C=C(N)[CH:39]=1.C([N:47](C(C)C)CC)(C)C.CC[O:55][C:56](C)=[O:57]>C(Cl)Cl>[NH2:47][C:7]1[CH:6]=[C:5]([NH:8][C:9]([CH:24]2[CH2:23][CH2:22][N:28]([C:56]([O:55][C:34]([CH3:35])([CH3:39])[CH3:33])=[O:57])[CH2:26][CH2:25]2)=[O:17])[CH:4]=[C:3]([C:18]([F:19])([F:20])[F:21])[CH:2]=1

Participants

7

Reactant 5

HCID 8857Ethyl AcetateHCID 677815-(Trifluoromethyl)benzene-1,3-diamineHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 13412531HCID 13412531, compound

Product 1

HCID 118223407HCID 118223407, compoundYield 40%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Mix the compound obtained in Step 1 (1.1 g, crude), HOBt (1.6 g, 12 mmol), 5-(trifluoromethyl)benzene-1,3-diamine (845 mg, 4.8 mmol) in DCM (16 mL), add diisopropylethylamine (1.55 g, 12 mmol), 1-ethyl-3-(3-dimethyllaminopropyl)carbodiimide hydrochloride (2.3 g, 12 mmol) and stir at room temperature for 17 hrs. TLC (PE:EtOAc=1:1) shows the reaction is complete. Remove the volatiles under reduced pressure, purify the residue by chromatography (silica gel, EOAc:PE=4:6) to give the title compound (600 mg, 40% two-step yield).

Workup

  1. customRemove the volatiles under reduced pressure
  2. custompurify the residue by chromatography (silica gel, EOAc:PE=4:6)

Sources & evidence

ORD record
ord-e130601e7f724ca69da8e6ebc4e8d7f7
Source dataset
uspto-grants-2016_06
Patent number
US09359338B2

Reaction notes

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