Trifluoroacetic acid → HCID 57468443, compound

HRID 1676213Notes

Reaction equation

HRID 1676213 reaction equation
C([NH:5][S:6]([C:9]1[CH:14]=[CH:13][C:12]([N:15]2[CH:20]=[CH:19][C:18]([O:21][CH:22]3[CH2:27][CH2:26][N:25]([C:28]4[N:33]=[CH:32][C:31]([CH2:34][CH2:35][CH3:36])=[CH:30][N:29]=4)[CH2:24][CH2:23]3)=[CH:17][C:16]2=[O:37])=[CH:11][CH:10]=1)(=[O:8])=[O:7])(C)(C)C.FC(F)(F)C(O)=O>C(Cl)Cl>[O:37]=[C:16]1[CH:17]=[C:18]([O:21][CH:22]2[CH2:27][CH2:26][N:25]([C:28]3[N:33]=[CH:32][C:31]([CH2:34][CH2:35][CH3:36])=[CH:30][N:29]=3)[CH2:24][CH2:23]2)[CH:19]=[CH:20][N:15]1[C:12]1[CH:11]=[CH:10][C:9]([S:6]([NH2:5])(=[O:7])=[O:8])=[CH:14][CH:13]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 57550100HCID 57550100, compound

Product 1

HCID 57468443HCID 57468443, compoundYield 53.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirring solution of N-tert-butyl-4-(2-oxo-4-(1-(5-propylpyrimidin-2-yl)piperidin-4-yloxy)pyridin-1(2H)-yl)benzenesulfonamide (23 mg, 0.044 mmol) in CH2Cl2 (1 mL) was added trifluoroaceticacid (0.4 mL, 5 mmol, Aldrich). The reaction was stirred at room temperature for 2 days and then concentrated in vacuo to a yellow oil. The oil was purified by flash chromatography (SiO2, 0 to 5% MeOH in CH2Cl2) to yield 11 mg of the desired product as an off-white solid. 1H NMR (400 MHz, CDCl3) δ ppm 8.18 (s, 2H), 8.03 (d, J=8.53 Hz, 2H), 7.54 (d, J=8.28 Hz, 2H), 7.23 (d, J=7.78 Hz, 1H), 6.07 (dd, J=7.65, 2.63 Hz, 1H), 6.03 (d, J=2.51 Hz, 1H), 4.56-4.65 (m, 1H), 4.16-4.25 (m, 2H), 3.60-3.71 (m, 2H), 2.42 (t, J=7.53 Hz, 2H), 2.04-2.14 (m, 2H), 1.80-1.90 (m, 2H), 1.53-1.64 (m, 2H), 0.95 (t, J=7.28 Hz, 3 H). MS (ESI) 470 (M+H).

Workup

  1. concentrationconcentrated in vacuo to a yellow oil
  2. customThe oil was purified by flash chromatography (SiO2, 0 to 5% MeOH in CH2Cl2)

Sources & evidence

ORD record
ord-04c48647ef084e7ea6c291881c28b1bf
Source dataset
uspto-grants-2011_08
Patent number
US08003796B2

Reaction notes

Loading…