Trifluoroacetic acid → HCID 18438697, compound

HRID 1988368Notes

Reaction equation

HRID 1988368 reaction equation
[Cl:1][C:2]1[CH:19]=[CH:18][C:17]([C:20]2[CH:21]=[N:22][N:23](CC3C=CC(OC)=CC=3)[CH:24]=2)=[CH:16][C:3]=1[C:4]([NH:6][CH2:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[Cl:15])=[O:5].FC(F)(F)C(O)=O.C1(OC)C=CC=CC=1>ClCCl>[Cl:1][C:2]1[CH:19]=[CH:18][C:17]([C:20]2[CH:24]=[N:23][NH:22][CH:21]=2)=[CH:16][C:3]=1[C:4]([NH:6][CH2:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[Cl:15])=[O:5]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acid2×HCID 7519Anisole2×HCID 18438695HCID 18438695, compound

Product 1

HCID 18438697HCID 18438697, compoundYield 112.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
110 °C

Procedure

To as solution of 2-chloro-N-[2-(2-chloro-phenyl)-ethyl]-5-[1-(4-methoxy-benzyl)-1H-pyrazol-4-yl]-benzamide (20 mg, 0.042 mmol) in dichloromethane (0.2 mL) was added trifluoroacetic acid (24 mg, 0.21 mmol) and anisole (45 mg, 0.42 mmol). The mixture was stirred at 110° C., for 16 h. A second portion of trifluoroacetic acid (0.2 mL) and anisole (45 μL) was added and the mixture was stirred at 110° C. for a further 6 h. The mixture was concentrated in vacuo to dryness and triturated with hexane to afford the title compound as an orange solid (17 mg). LCMS (m/z) 358.5 M+1.

Workup

  1. stirringthe mixture was stirred at 110° C. for a further 6 h
  2. concentrationThe mixture was concentrated in vacuo to dryness
  3. customtriturated with hexane

Sources & evidence

ORD record
ord-35db68915cfe4147a2f37acf3b8bea2d
Source dataset
uspto-grants-2009_06
Patent number
US07553972B2

Reaction notes

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