Trifluoroacetic acid → HCID 136644914, compound

HRID 59510Notes

Reaction equation

HRID 59510 reaction equation
[CH:1]1([NH:7][NH:8]C(OC(C)(C)C)=O)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[Cl:16][C:17]1[C:22]([C:23]([N:25]=[C:26]=[O:27])=O)=[C:21]([F:28])[C:20]([CH2:29][NH:30][C:31](=[O:36])[C:32]([CH3:35])([CH3:34])[CH3:33])=[CH:19][CH:18]=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[Cl:16][C:17]1[CH:18]=[CH:19][C:20]([CH2:29][NH:30][C:31](=[O:36])[C:32]([CH3:35])([CH3:34])[CH3:33])=[C:21]([F:28])[C:22]=1[C:23]1[NH:25][C:26](=[O:27])[N:7]([CH:1]2[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]2)[N:8]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 11218168Tert-butyl 2-cyclohexylhydrazinecarboxylateHCID 900197456-Chloro-2-fluoro-3-(pivalamidomethyl)benzoyl isocyanate

Product 1

HCID 136644914HCID 136644914, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The title compound was prepared by following the procedure as described for Example-83 by using tert-butyl 2-(cyclohexyl)hydrazinecarboxylate (Intermediate-64, 0.050 g, 0.23 mmol), 6-chloro-2-fluoro-3-(pivalamidomethyl)benzoyl isocyanate (Intermediate-51, 0.225 g, 0.70 mmol), DCM (10 mL) and TFA (3 mL) to afford 0.015 g of pure product. NMR (400 MHz, DMSO d6): δ 1.13 (s, 9H), 1.22-1.23 (m, 2H), 1.30-1.37 (m, 2H), 1.62-1.64 (m, 2H), 1.78-1.81 (m, 4H), 3.90-3.92 (m, 1H), 4.27-4.28 (d, J=4.8 Hz, 2H), 7.37-7.41 (t, 1H), 7.46-7.48 (d, 1H), 8.17 (br s, 1H); MS (m/z): 409.36 (M+H+).

Sources & evidence

ORD record
ord-34bb220f2b9f45db86d3ee291462c8cd
Source dataset
uspto-grants-2016_09
Patent number
US09439890B2

Reaction notes

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