HCID 44220043, compound → HCID 44220233, compound

HRID 549972Notes

Reaction equation

HRID 549972 reaction equation
C([N:5]1[CH:9]=[C:8]([S:10]([F:15])([F:14])([F:13])([F:12])[F:11])[C:7]([CH2:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[C:6]1[C:24]([O:26][CH3:27])=[O:25])(C)(C)C>C(S(O)(=O)=O)(F)(F)F.C(Cl)Cl>[F:14][S:10]([F:11])([F:12])([F:13])([F:15])[C:8]1[C:7]([CH2:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[C:6]([C:24]([O:26][CH3:27])=[O:25])[NH:5][CH:9]=1

Participants

4

Reactant 1

HCID 44220043HCID 44220043, compound

Product 1

HCID 44220233HCID 44220233, compoundYield 78%

Reagents, catalysts & solvents 2

HCID 62406Trifluoromethanesulfonic acidCatalystHCID 6344DichloromethaneSolvent

Procedure

Two drops of CF3SO3H was added to a flask containing 80 mg 6a and 2 mL CH2Cl2 at RT, and the mixture was stirred for about 2 h (monitored by TLC). The mixture was purified directly by column chromatograph to obtain 7 as a white solid (78%): mp 165-167° C., 1H NMR, δ 2.78-2.84 (dd, J=8.1 & 4.2 Hz, 2H), 3.16-3.22 (dd, J=8.1 & 4.2 Hz, 2H), 3.92 (s, 3H), 7.19-7.34 (m, 6H), 9.34 (s, 1H); 13C NMR, δ 28.38, 37.49, 52.12, 118.81 (m), 122.02 (m), 126.19, 128.00 (m), 128.58, 128.61, 138.50 (m), 142.07, 161.26; 19F NMR, δ 88.87 (p, J=148 Hz, 1H), 73.56 (d, J=148 Hz, 4H); HRMS, calc for C14H14F5NO2S, 355.0665; found, 355.0648; Anal, calc for C14H14F5NO2S: C, 47.32; H, 3.97; N, 3.94; found: C, 47.04; H, 3.68; N, 3.86.

Workup

  1. customThe mixture was purified directly by column chromatograph

Sources & evidence

ORD record
ord-3d690adcaed94bec8936689e083d6c88
Source dataset
uspto-grants-2011_05
Patent number
US07943787B2

Reaction notes

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