Triethylamine → HCID 86707214, compound

HRID 2408227Notes

Reaction equation

HRID 2408227 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:18]2[C:19]([NH2:24])=[CH:20][CH:21]=[CH:22][CH:23]=2)[CH:5]=[C:6]([F:17])[C:7]=1[N:8]1[CH:12]=[CH:11][C:10]([C:13]([F:16])([F:15])[F:14])=[N:9]1.[Cl:25][C:26]1[C:31]([C:32](Cl)=[O:33])=[CH:30][CH:29]=[CH:28][N:27]=1.C(N(CC)CC)C>ClCCl>[Cl:25][C:26]1[C:31]([C:32]([NH:24][C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=2[C:4]2[CH:5]=[C:6]([F:17])[C:7]([N:8]3[CH:12]=[CH:11][C:10]([C:13]([F:16])([F:15])[F:14])=[N:9]3)=[C:2]([F:1])[CH:3]=2)=[O:33])=[CH:30][CH:29]=[CH:28][N:27]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 27745412-Chloronicotinoyl chlorideHCID 86707215HCID 86707215, compound2×

Product 1

HCID 86707214HCID 86707214, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 3′,5′-difluoro-4′-[3-(trifluoromethyl)-1H-pyrazol-1-yl][1,1′-biphenyl]-2-amine (i.e. the product of Step D; 0.17 g, 0.52 mmol), 2-chloro-3-pyridinecarbonyl chloride (0.092 g, 0.52 mmol) and triethylamine (0.050 g, 0.52 mmol) in dichloromethane (5 mL) was stirred for 16 h at room temperature. The reaction mixture was then concentrated under reduced pressure, and the residue was purified by medium pressure liquid chromatography on silica gel eluted with 0 to 100% ethyl acetate in hexanes. The resulting solid was triturated with 1-chlorobutane and hexanes to yield the title compound (0.090 g), a compound of the present invention.

Workup

  1. concentrationThe reaction mixture was then concentrated under reduced pressure
  2. customthe residue was purified by medium pressure liquid chromatography on silica gel
  3. washeluted with 0 to 100% ethyl acetate in hexanes
  4. customThe resulting solid was triturated with 1-chlorobutane and hexanes

Sources & evidence

ORD record
ord-57a45d4cdb174d8381584cfd22cdb458
Source dataset
uspto-grants-2014_08
Patent number
US08815772B2

Reaction notes

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