Trifluoroacetic acid → HCID 67126550, compound

HRID 2168084Notes

Reaction equation

HRID 2168084 reaction equation
[NH:1]1[C:5]2=[N:6][CH:7]=[C:8]([O:10][C:11]3[CH:46]=[C:45]([N:47]4[CH2:52][CH2:51][N:50]([CH2:53][C:54]5[CH2:59][CH2:58][C:57]([CH3:61])([CH3:60])[CH2:56][C:55]=5[C:62]5[CH:67]=[CH:66][C:65]([Cl:68])=[CH:64][CH:63]=5)[CH2:49][CH2:48]4)[CH:44]=[CH:43][C:12]=3[C:13]([NH:15][S:16]([C:19]3[CH:24]=[CH:23][C:22]([NH:25][CH2:26][CH2:27][CH2:28][N:29]([CH:37]4[CH2:39][CH2:38]4)C(=O)OC(C)(C)C)=[C:21]([N+:40]([O-:42])=[O:41])[CH:20]=3)(=[O:18])=[O:17])=[O:14])[CH:9]=[C:4]2[CH:3]=[CH:2]1.FC(F)(F)C(O)=O>ClCCl>[Cl:68][C:65]1[CH:64]=[CH:63][C:62]([C:55]2[CH2:56][C:57]([CH3:60])([CH3:61])[CH2:58][CH2:59][C:54]=2[CH2:53][N:50]2[CH2:51][CH2:52][N:47]([C:45]3[CH:44]=[CH:43][C:12]([C:13]([NH:15][S:16]([C:19]4[CH:24]=[CH:23][C:22]([NH:25][CH2:26][CH2:27][CH2:28][NH:29][CH:37]5[CH2:38][CH2:39]5)=[C:21]([N+:40]([O-:42])=[O:41])[CH:20]=4)(=[O:18])=[O:17])=[O:14])=[C:11]([O:10][C:8]4[CH:9]=[C:4]5[CH:3]=[CH:2][NH:1][C:5]5=[N:6][CH:7]=4)[CH:46]=3)[CH2:48][CH2:49]2)=[CH:67][CH:66]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 87279768HCID 87279768, compound

Product 1

HCID 67126550HCID 67126550, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of EXAMPLE 291D (2.56 g) in dichloromethane (10 mL) was added trifluoroacetic acid (10 mL). The mixture was stirred for 2 hours. The mixture was concentrated under vacuum and the residue was dissolved in dichloromethane (300 mL) and washed with aqueous NaHCO3, water, and brine and dried over Na2SO4. Filtration and evaporation of the solvent gave the crude product. The title compound was obtained by dissolving 200 mg of the crude material in dimethylsulfoxide/methanol (1:1, 10 mL) and loaded on Gilson, C18 (100A) 250×121.2 mm (10 micron), eluting with 30% acetonitrile to 65% acetonitrile over 40 minutes. 1H NMR (300 MHz, dimethylsulfoxide-d6) δ 11.54 (s, 1 H), 8.43 (m, 2 H), 7.94 (d, 1 H), 7.71 (dd, 1 H), 7.57 (d, 1 H), 7.43 (m, 1 H), 7.34 (m, 3 H), 7.05 (d, 2 H), 6.90 (d, 1 H), 6.63 (dd, 1 H), 6.29 (d, 2 H), 3.43 (m, 2 H), 2.96 (m, 6 H), 2.73 (m, 2 H), 2.22 (m, 7 H), 1.87 (m, 4 H), 1.38 (m, 3 H), 0.94 (m, 6 H), 0.62 (m, 4 H).

Workup

  1. concentrationThe mixture was concentrated under vacuum
  2. dissolutionthe residue was dissolved in dichloromethane (300 mL)
  3. washwashed with aqueous NaHCO3, water, and brine
  4. dry with materialdried over Na2SO4
  5. filtrationFiltration and evaporation of the solvent
  6. customgave the crude product

Sources & evidence

ORD record
ord-3d035be30f2e4ee88231dd4975ba1478
Source dataset
uspto-grants-2015_06
Patent number
US09045475B2

Reaction notes

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