HCID 70147406, compound → HCID 178438986, compound

HRID 1815500Notes

Reaction equation

HRID 1815500 reaction equation
[CH:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[S:10][C:11]1[CH:16]=[CH:15][C:14](/[CH:17]=[CH:18]/[C:19]([N:21]2[CH2:26][CH2:25][CH2:24][CH:23]([C:27]3[N:28]=[N:29][N:30](COC)[N:31]=3)[CH2:22]2)=[O:20])=[CH:13][C:12]=1[N+:35]([O-:37])=[O:36])([CH3:3])[CH3:2]>C(O)(C(F)(F)F)=O>[CH:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[S:10][C:11]1[CH:16]=[CH:15][C:14](/[CH:17]=[CH:18]/[C:19]([N:21]2[CH2:26][CH2:25][CH2:24][CH:23]([C:27]3[NH:28][N:29]=[N:30][N:31]=3)[CH2:22]2)=[O:20])=[CH:13][C:12]=1[N+:35]([O-:37])=[O:36])([CH3:3])[CH3:2]

Participants

3

Reactant 1

HCID 70147406HCID 70147406, compound

Product 1

HCID 178438986HCID 178438986, compoundYield 74.6%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

The compound from Example 279 (75 mg, 0.14 mmol) was dissolved in 1 mL of neat TFA and left at ambient temperature for overnight. The reagent was then removed in vacuo and the residue was evaporated twice with benzene. The crude product was purified using Gilson Preparative HPLC as described in Example 38B to give the title compound as a light-yellow solid (50 mg, 72%); 1H NMR (CDCl3, 300 MHz) δ 1.17 (d, J=6.5 Hz, 6H), 1.25-1.39 (m, 1H), 1.69-1.81 (m, 1H), 2.09 (br s, 1H), 2.14-2.30 (m, 1H), 2.57-2.71 (m, 1H), 3.35-3.66 (m, 3H), 3.90-4.03 (m, 1H), 4.66-4.78 (m, 1H), 6.73 (d, J=8.7 Hz, 1H), 6.86 (d, J=15.3 Hz, 1H), 7.32 (dd, J=2.1, 6.9 Hz, 1H), 7.42 (dd, J=2.1, 8.7 Hz, 1H), 7.47-7.57 (m, 3H), 7.76 (d, J=15.3 Hz, 1H), 8.46 (d, J=2.1 Hz, 1H). MS (ESI+) (M+H)+ at m/z 479. Anal. Calcd for C24H26N6O3S.0.28 H2O: C, 59.61; H, 5.54; N, 17.38. Found: C, 59.71; H, 5.44; N, 16.99.

Workup

  1. customThe reagent was then removed in vacuo
  2. customthe residue was evaporated twice with benzene
  3. customThe crude product was purified

Sources & evidence

ORD record
ord-06dfe75c198640328c6162606bbaf64b
Source dataset
uspto-grants-2005_04
Patent number
US06878700B1

Reaction notes

Loading…