Trifluoroacetic acid → HCID 67225689, compound

HRID 2045113Notes

Reaction equation

HRID 2045113 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([S:17]([NH:20][C:21](=[O:79])[C:22]2[CH:27]=[CH:26][C:25]([N:28]3[CH2:33][CH2:32][N:31]([CH2:34][C:35]4[CH2:40][C:39]([F:42])([F:41])[CH2:38][CH2:37][C:36]=4[C:43]4[CH:48]=[CH:47][C:46]([Cl:49])=[CH:45][CH:44]=4)[CH2:30][CH2:29]3)=[CH:24][C:23]=2[O:50][C:51]2[CH:59]=[CH:58][CH:57]=[C:56]3[C:52]=2[CH:53]=[N:54][N:55]3C(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(=[O:19])=[O:18])[CH:5]=[N:6][C:7]=1[O:8][CH2:9][C:10]1([F:16])[CH2:15][CH2:14][O:13][CH2:12][CH2:11]1.FC(F)(F)C(O)=O>ClCCl>[NH:55]1[C:56]2[C:52](=[C:51]([O:50][C:23]3[CH:24]=[C:25]([N:28]4[CH2:33][CH2:32][N:31]([CH2:34][C:35]5[CH2:40][C:39]([F:41])([F:42])[CH2:38][CH2:37][C:36]=5[C:43]5[CH:44]=[CH:45][C:46]([Cl:49])=[CH:47][CH:48]=5)[CH2:30][CH2:29]4)[CH:26]=[CH:27][C:22]=3[C:21]([NH:20][S:17]([C:4]3[CH:5]=[N:6][C:7]([O:8][CH2:9][C:10]4([F:16])[CH2:11][CH2:12][O:13][CH2:14][CH2:15]4)=[C:2]([Cl:1])[CH:3]=3)(=[O:19])=[O:18])=[O:79])[CH:59]=[CH:58][CH:57]=2)[CH:53]=[N:54]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 87315513HCID 87315513, compound

Product 1

HCID 67225689HCID 67225689, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of EXAMPLE 521I (0.24 g) dichloromethane (1 mL) was added trifluoroacetic acid (0.5 mL). After stirring for 1 hour, the reaction was concentrated, dissolved in dichloromethane (5 mL) and quenched with saturated NaHCO3 (5 mL). The reaction was diluted with water (10 mL) and saturated NaHCO3 (15 mL) and the product extracted into dichloromethane (2×25 mL). The combined organics were washed with brine (25 mL), dried over magnesium sulfate, filtered, and concentrated. The residue was loaded onto silica gel (Reveleris 40 g) and eluted using a gradient of 0.5% to 3% methanol/dichloromethane over 30 minutes (flow=40 ml/minutes). The product was collected, concentrated, dissolved in acetonitrile and concentrated, and dried in vacuum oven at 75° C. overnight to give the title compound. 1H NMR (300 MHz, dimethylsulfoxide-d6) δ 13.12 (s, 1H), 12.24-11.44 (m, 1H), 8.31 (d, 1H), 7.91 (d, 1H), 7.83 (s, 1H), 7.57 (d, 1H), 7.40 (d, 2H), 7.13 (d, 4H), 6.81 (dd, 1H), 6.56 (d, 1H), 6.16 (dd, 1H), 4.52 (d, 2H), 3.79 (dt, 2H), 3.70-3.51 (m, 2H), 3.20 (s, 4H), 2.76 (dd, 4H), 2.49 (m, 8H), 2.02-1.71 (m, 4H).

Workup

  1. concentrationthe reaction was concentrated
  2. dissolutiondissolved in dichloromethane (5 mL)
  3. customquenched with saturated NaHCO3 (5 mL)
  4. additionThe reaction was diluted with water (10 mL) and saturated NaHCO3 (15 mL)
  5. extractionthe product extracted into dichloromethane (2×25 mL)
  6. washThe combined organics were washed with brine (25 mL)
  7. dry with materialdried over magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated
  10. washeluted
  11. customover 30 minutes
  12. customThe product was collected
  13. concentrationconcentrated
  14. dissolutiondissolved in acetonitrile
  15. concentrationconcentrated
  16. customdried in vacuum oven at 75° C. overnight

Sources & evidence

ORD record
ord-add3bdbea83d42d59b72c615feb45ea0
Source dataset
uspto-grants-2013_11
Patent number
US08586754B2

Reaction notes

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