HCID 68649047, compound → HCID 59604051, compound

HRID 219594Notes

Reaction equation

HRID 219594 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[C:12]([C:13]2[CH:18]=[CH:17][N:16]=[CH:15][CH:14]=2)=[C:11]([C:19]2[O:23][N:22]=[C:21]([C:24]3[CH:32]=[C:31]4[C:27]([CH2:28][CH2:29][N:30]4C(=O)C)=[CH:26][CH:25]=3)[N:20]=2)[N:10]=[N:9]1>Cl.CO>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[C:12]([C:13]2[CH:14]=[CH:15][N:16]=[CH:17][CH:18]=2)=[C:11]([C:19]2[O:23][N:22]=[C:21]([C:24]3[CH:32]=[C:31]4[C:27]([CH2:28][CH2:29][NH:30]4)=[CH:26][CH:25]=3)[N:20]=2)[N:10]=[N:9]1

Participants

4

Reactant 1

HCID 68649047HCID 68649047, compound

Product 1

HCID 59604051HCID 59604051, compound

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 887MethanolSolvent

Procedure

The title compound was prepared following the procedure described for Example 156, but using 1-(6-(5-(1-(2-fluorophenyl)-5-(pyridin-4-yl)-1H-1,2,3-triazol-4-yl)-1,2,4-oxadiazol-3-yl)indolin-1-yl)ethanone, obtained in Step 1, (101 mg; 0.22 mmol). The solvent was removed in vacuo to afford a purple oil which was dissolved in HCl (1 M, 1 mL) and MeOH (1 mL). The solution was passed through an SCX column eluting with MeOH (50 mL) followed by NH3 (1 M in MeOH, 50 mL). The solvent was removed in vacuo from the fractions containing product to afford Example 157 as a yellow solid. 1H NMR: (DMSO-d5, 400 MHz) δ 8.74 (2H, d, J=5.2 Hz), 7.90 (1H, t, J=7.7 Hz), 7.77-7.68 (1H, m), 7.60 (2H, d, J=5.2 Hz), 7.55-7.41 (2H, m), 7.24-7.15 (2H, m), 7.10-6.95 (1H, m), 5.89 (1H, s), 3.56-3.44 (2H, m), 3.01 (2H, t, J=8.6 Hz). LC/MS (Method C): 426 (M+H)+. HPLC (Method I) Rt 14.83 min (Purity: 95.2%).

Workup

  1. customobtained in Step 1, (101 mg; 0.22 mmol)
  2. customThe solvent was removed in vacuo
  3. customto afford a purple oil which
  4. washeluting with MeOH (50 mL)
  5. customThe solvent was removed in vacuo from the fractions
  6. additioncontaining product

Sources & evidence

ORD record
ord-28eb9fd532474bdda0ad08327e0cea7a
Source dataset
uspto-grants-2012_06
Patent number
US08202856B2

Reaction notes

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