HCID 58269325, compound → HCID 58269182, compound

HRID 239685Notes

Reaction equation

HRID 239685 reaction equation
C(OC(=O)[NH:7][CH2:8][C:9]1[S:10][C:11]([C:14]2[C:22]3[C:17](=[N:18][CH:19]=[N:20][C:21]=3[NH2:23])[N:16]([CH:24]([C:26]3[O:27][C:28]4[C:33]([C:34](=[O:43])[C:35]=3[C:36]3[CH:41]=[CH:40][CH:39]=[C:38]([F:42])[CH:37]=3)=[CH:32][CH:31]=[CH:30][CH:29]=4)[CH3:25])[N:15]=2)=[CH:12][CH:13]=1)(C)(C)C>ClCCl.C(O)(C(F)(F)F)=O>[NH2:23][C:21]1[N:20]=[CH:19][N:18]=[C:17]2[N:16]([CH:24]([C:26]3[O:27][C:28]4[C:33]([C:34](=[O:43])[C:35]=3[C:36]3[CH:41]=[CH:40][CH:39]=[C:38]([F:42])[CH:37]=3)=[CH:32][CH:31]=[CH:30][CH:29]=4)[CH3:25])[N:15]=[C:14]([C:11]3[S:10][C:9]([CH2:8][NH2:7])=[CH:13][CH:12]=3)[C:22]=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-f3c9fd4d3e1d40ac9fce7d22f7141253
Source dataset
uspto-grants-2014_02
Patent number
US08642607B2

Reaction notes

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