Diisopropylethylamine → HCID 71164809, compound

HRID 1622572Notes

Reaction equation

HRID 1622572 reaction equation
Cl.[F:2][C:3]1[CH:4]=[C:5]([C@@H:14]([C:16]2[C:21]([F:22])=[CH:20][CH:19]=[CH:18][N:17]=2)[NH2:15])[CH:6]=[CH:7][C:8]=1[O:9][C:10]([F:13])([F:12])[F:11].[N:23]([C:26]1[CH:36]=[CH:35][C:29]([C:30]([O:32][CH2:33][CH3:34])=[O:31])=[CH:28][CH:27]=1)=[C:24]=[O:25].C(N(C(C)C)C(C)C)C>C(Cl)Cl>[F:2][C:3]1[CH:4]=[C:5]([C@@H:14]([C:16]2[C:21]([F:22])=[CH:20][CH:19]=[CH:18][N:17]=2)[NH:15][C:24](=[O:25])[NH:23][C:26]2[CH:36]=[CH:35][C:29]([C:30]([O:32][CH2:33][CH3:34])=[O:31])=[CH:28][CH:27]=2)[CH:6]=[CH:7][C:8]=1[O:9][C:10]([F:13])([F:12])[F:11]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 589805Ethyl 4-isocyanatobenzoateHCID 86687985(S)-(3-fluoro-4-(trifluoromethoxy)phenyl)(3-fluoropyridin-2-yl)methanamine hydrochloride2×

Product 1

HCID 71164809HCID 71164809, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (S)-(3-fluoro-4-(trifluoromethoxy)phenyl)(3-fluoropyridin-2-yl)methanamine hydrochloride (Intermediate 39) (112 mg, 0.329 mmol) and DCM (3 mL) was added ethyl 4-isocyanatobenzoate (65 mg, 0.340 mmol) and N-ethyl-N-isopropylpropan-2-amine (0.172 mL, 0.986 mmol). The solution was stirred at rt. After 20 minutes, the reaction product was adsorbed onto a plug of silica gel and chromatographed through a Redi-Sep®pre-packed silica gel column (4 g), eluting with 70% to 90% EtOAc in hexane, to provide the title compound as a white solid.

Workup

  1. customchromatographed through a Redi-Sep®pre-packed silica gel column (4 g)
  2. washeluting with 70% to 90% EtOAc in hexane

Sources & evidence

ORD record
ord-ea3c62361d7f4e47ac972e6e855937ee
Source dataset
uspto-grants-2014_07
Patent number
US08778941B2

Reaction notes

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