Trifluoroacetic acid → HCID 136246000, compound

HRID 59497Notes

Reaction equation

HRID 59497 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH:9][NH:10]C(OC(C)(C)C)=O)[CH:5]=[CH:6][C:7]=1[Cl:8].[Cl:18][C:19]1[C:24]([C:25]([N:27]=[C:28]=[O:29])=O)=[C:23]([F:30])[C:22]([CH2:31][NH:32][C:33](=[O:38])[C:34]([CH3:37])([CH3:36])[CH3:35])=[CH:21][CH:20]=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[Cl:18][C:19]1[CH:20]=[CH:21][C:22]([CH2:31][NH:32][C:33](=[O:38])[C:34]([CH3:37])([CH3:36])[CH3:35])=[C:23]([F:30])[C:24]=1[C:25]1[NH:27][C:28](=[O:29])[N:9]([C:4]2[CH:5]=[CH:6][C:7]([Cl:8])=[C:2]([Cl:1])[CH:3]=2)[N:10]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 900197456-Chloro-2-fluoro-3-(pivalamidomethyl)benzoyl isocyanateHCID 90065722HCID 90065722, compound

Product 1

HCID 136246000HCID 136246000, compoundYield 7.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of tert-butyl 2-(3,4-dichlorophenyl)hydrazinecarboxylate (Intermediate-52, 0.060 g, 0.21 mmol) in DCM (10 mL) was added solution of 6-chloro-2-fluoro-3-(pivalamidomethyl)benzoyl isocyanate (Intermediate-51, 0.101 g, 0.32 mmol) in DCM and the reaction mixture was stirred for 20 h at room temperature, followed by addition of TFA (3 mL) and further stirred for 20 h at room temperature. The reaction mass was quenched in water, extracted with DCM and concentrated to afford crude product which was purified by column chromatography eluting with MeOH:DCM to afford 0.007 g of pure product. 1H NMR (300 MHz, CDCl3): δ 1.20 (s, 9H), 4.44 (d, J=5.4 Hz, 2H), 6.20 (m, 1H), 7.29 (m, 1H), 7.41-7.49 (m, 2H), 7.91 (d, J=8.1 Hz, 1H), 8.15 (s, 1H); MS (m/z): 471.26 (M+).

Workup

  1. stirringfurther stirred for 20 h at room temperature
  2. customThe reaction mass was quenched in water
  3. extractionextracted with DCM
  4. concentrationconcentrated
  5. customto afford crude product which
  6. customwas purified by column chromatography
  7. washeluting with MeOH

Sources & evidence

ORD record
ord-f11726a7fafc4496a0c0f2ef81705018
Source dataset
uspto-grants-2016_09
Patent number
US09439890B2

Reaction notes

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