HCID 58269325, compound → HCID 58269182, compound

HRID 1476236Notes

Reaction equation

HRID 1476236 reaction equation
[NH2:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]2[N:8]([CH:25]([C:27]3[O:28][C:29]4[C:34]([C:35](=[O:44])[C:36]=3[C:37]3[CH:42]=[CH:41][CH:40]=[C:39]([F:43])[CH:38]=3)=[CH:33][CH:32]=[CH:31][CH:30]=4)[CH3:26])[N:9]=[C:10]([C:11]3[S:15][C:14]([CH2:16][NH:17]C(=O)OC(C)(C)C)=[CH:13][CH:12]=3)[C:3]=12>ClCCl.C(O)(C(F)(F)F)=O>[NH2:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]2[N:8]([CH:25]([C:27]3[O:28][C:29]4[C:34]([C:35](=[O:44])[C:36]=3[C:37]3[CH:42]=[CH:41][CH:40]=[C:39]([F:43])[CH:38]=3)=[CH:33][CH:32]=[CH:31][CH:30]=4)[CH3:26])[N:9]=[C:10]([C:11]3[S:15][C:14]([CH2:16][NH2:17])=[CH:13][CH:12]=3)[C:3]=12

Participants

4

Reactant 1

HCID 58269325HCID 58269325, compound

Product 1

HCID 58269182HCID 58269182, compoundYield 51.3%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 6422Trifluoroacetic acidSolvent

Procedure

To a solution of Example 102 (0.070 g, 0.114 mmoles) in dichloromethane (3 ml), TFA (0.1 ml) was added under nitrogen atmosphere stirred at room temperature. After 3 h, the reaction mixture was concentrated, neutralised with sodium bicarbonate solution and extracted with ethyl acetate. The organic layer was dried over sodium sulphate and concentrated under reduced pressure. The crude product was purified by column chromatography with methanol: dichloromethane to afford the title compound as yellow solid (0.030 g, 51% yield). MP: 275-278° C. 1H-NMR (δ ppm, DMSO-d6, 400 MHz): δ 8.06(s,1H), 8.05(dd, J=7.9,1.5 Hz, 1H), 7.85(m,1H), 7.66(d, J=8.3 Hz, 1H), 7.53(t, J=7.2 Hz, 1H), 7.28(m, 2H), 7.09(d, J=3.5 Hz, 1H), 7.05(dt, J=8.7,2.4 Hz, 1H), 6.92(br s,2H), 6.02(q, J=7.1 Hz, 1H),4.03(s,2H), 1.87(d, J=7.1 Hz, 3H). Mass: 513.27(M++1).

Workup

  1. concentrationthe reaction mixture was concentrated
  2. extractionextracted with ethyl acetate
  3. dry with materialThe organic layer was dried over sodium sulphate
  4. concentrationconcentrated under reduced pressure
  5. customThe crude product was purified by column chromatography with methanol

Sources & evidence

ORD record
ord-df2266bf57044d26b109860f64b54f4e
Source dataset
uspto-grants-2015_04
Patent number
US09018375B2

Reaction notes

Loading…