HCID 86647913, compound → HCID 53250581, compound

HRID 1043221Notes

Reaction equation

HRID 1043221 reaction equation
C(OC([N:8](C(OC(C)(C)C)=O)[C:9]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][C:16]=2[O:18][C:19]2[CH:24]=[C:23]([N:25]3[CH2:30][CH2:29][N:28]([CH2:31][C:32]4[CH2:37][CH2:36][C:35]([CH3:39])([CH3:38])[CH2:34][C:33]=4[C:40]4[CH:45]=[CH:44][C:43]([Cl:46])=[CH:42][CH:41]=4)[CH2:27][CH2:26]3)[CH:22]=[CH:21][C:20]=2[C:47](=[O:70])[NH:48][S:49]([C:52]2[CH:57]=[CH:56][C:55]([NH:58][CH2:59][C:60]3([F:66])[CH2:65][CH2:64][O:63][CH2:62][CH2:61]3)=[C:54]([N+:67]([O-:69])=[O:68])[CH:53]=2)(=[O:51])=[O:50])[N:11](C(OC(C)(C)C)=O)[N:10]=1)=O)(C)(C)C>ClCCl.FC(F)(F)C(O)=O>[NH2:8][C:9]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][C:16]=2[O:18][C:19]2[CH:24]=[C:23]([N:25]3[CH2:30][CH2:29][N:28]([CH2:31][C:32]4[CH2:37][CH2:36][C:35]([CH3:39])([CH3:38])[CH2:34][C:33]=4[C:40]4[CH:41]=[CH:42][C:43]([Cl:46])=[CH:44][CH:45]=4)[CH2:27][CH2:26]3)[CH:22]=[CH:21][C:20]=2[C:47]([NH:48][S:49]([C:52]2[CH:57]=[CH:56][C:55]([NH:58][CH2:59][C:60]3([F:66])[CH2:65][CH2:64][O:63][CH2:62][CH2:61]3)=[C:54]([N+:67]([O-:69])=[O:68])[CH:53]=2)(=[O:51])=[O:50])=[O:70])[NH:11][N:10]=1

Participants

3

Reactant 1

HCID 86647913HCID 86647913, compound

Product 1

HCID 53250581HCID 53250581, compound

Reagents, catalysts & solvents 1

HCID 21863450Trifluoroacetic acid methylene chlorideSolvent

Procedure

The crude product of EXAMPLE 428F (0.10 g) was treated with 1:1 dichloromethane/trifluoroacetic acid (10 mL). The reaction was stirred for 2 hours. The solvents were removed, and the residue was purified by reverse phase Gilson Prep HPLC system with a Phenomenex prep column (Luna, 5 μA, C18(2), 250×21.20 mm, 5 Å) eluting with 20-80% acetonitrile in water with 0.1% trifluoroacetic acid. Fractions containing product were concentrated, and the concentrate was diluted with dichloromethane, neutralized with aqueous NaHCO3, dried over Na2SO4, filtered, and concentrated. 1H NMR (500 MHz, dimethylsulfoxide-d6) δ 11.47 (s, 1H), 8.58 (t, 1H), 8.40 (d, 1H), 7.49-7.53 (m, 2H), 7.36 (d, 2H), 7.06 (d, 2H), 7.01 (d, 1H), 6.88 (t, 1H), 6.88 (d, 2H), 6.49 (d, 1H), 5.69 (s, 1H), 3.68-3.79 (m, 4H), 3.52-3.56 (m, 2H), 3.17 (br s, 4H), 2.81 (br s, 2H), 2.17-2.25 (m, 6H), 1.97 (s, 2H), 1.77-1.87 (m, 4H), 1.40 (t, 2H), 0.94 (s, 6H).

Workup

  1. customThe solvents were removed
  2. customthe residue was purified by reverse phase Gilson Prep HPLC system with a Phenomenex prep column (Luna, 5 μA, C18(2), 250×21.20 mm, 5 Å)
  3. washeluting with 20-80% acetonitrile in water with 0.1% trifluoroacetic acid
  4. additionFractions containing product
  5. concentrationwere concentrated
  6. additionthe concentrate was diluted with dichloromethane
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-43fcd91ad0504d1686ef0ebc7a914361
Source dataset
uspto-grants-2013_10
Patent number
US08557983B2

Reaction notes

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