Trifluoroacetic acid → HCID 136246000, compound

HRID 508989Notes

Reaction equation

HRID 508989 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-7e07b868fa1e47d8a358d1f5cd3820f0
Source dataset
uspto-grants-2015_08
Patent number
US09096545B2

Reaction notes

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