HCID 69630218, compound → HCID 9850545, compound

HRID 1792845Notes

Reaction equation

HRID 1792845 reaction equation
[C:1]1([S:7]([NH:10][CH:11]([C:28](=[O:40])[NH:29][CH2:30][CH2:31][CH2:32][CH2:33][C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[CH2:12][C:13]2[CH:21]=[C:20](Cl)[C:19]([O:23][CH2:24][C:25]([OH:27])=[O:26])=[C:18]3[C:14]=2[CH:15]=[N:16][NH:17]3)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1>CO.[Pd]>[C:1]1([S:7]([NH:10][CH:11]([C:28](=[O:40])[NH:29][CH2:30][CH2:31][CH2:32][CH2:33][C:34]2[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=2)[CH2:12][C:13]2[CH:21]=[CH:20][C:19]([O:23][CH2:24][C:25]([OH:27])=[O:26])=[C:18]3[C:14]=2[CH:15]=[N:16][NH:17]3)(=[O:9])=[O:8])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 1

HCID 69630218HCID 69630218, compound

Product 1

HCID 9850545HCID 9850545, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

{4-[2-Benzenesulfonylamino-2-(4-phenyl-butylcarbamoyl)-ethyl]-6-chloro-1H-indazol-7-yloxy}-acetic acid (8.0 mg, 0.014 mmol) is dissolved in MeOH (1.5 mL) and 10% Pd/C (5 mg) is added. The reaction is purged with N2 and then with H2. The reaction is rapidly stirred and monitored by HPLC until complete (approximately 30 h). The reaction is filtered through celite and washed with MeOH to provide {4-[2-benzenesulfonylamino-2-(4-phenyl-butylcarbamoyl)-ethyl]-1H-indazol-7-yloxy}-acetic acid. 1H NMR (500 MHz, MeOH-d4) δ 7.88 (s, 1H), 7.49–7.47 (d, 2H), 7.40 (dd, 1H), 7.25–7.21 (m, 4H), 7.15–7.13 (m, 3H), 6.70 (d, 1H), 6.49 (d, 1H), 5.37 (m, 1H), 4.45 (s, 2H), 3.97 (t, 1H), 3.6 (obs, 1H), 3.14 (dd, 1H), 3.07–3.02 (m, 2H), 2.94–2.89 (m, 2H), 2.53 (t, 2H), 1.45–1.39 (m, 2H), 1.28–1.22 (m, 2H); MS (ESI+) m/z 551 (M+H).

Workup

  1. customThe reaction is purged with N2
  2. custommonitored by HPLC until complete (approximately 30 h)
  3. filtrationThe reaction is filtered through celite
  4. washwashed with MeOH

Sources & evidence

ORD record
ord-07c91a5812cd47a1a871308ec1152428
Source dataset
uspto-grants-2006_07
Patent number
US07078425B2

Reaction notes

Loading…