HCID 58649722, compound → HCID 58649720, compound

HRID 1829912Notes

Reaction equation

HRID 1829912 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][O:11][CH2:10][C@@H:9]1[CH2:14][O:15][C:16](=[O:45])[NH:17][C:18]1[C:19]([CH3:44])=[C:20]2[N:25]([CH:26]=1)[N:24]=[CH:23][N:22]=[C:21]2[NH:27][C:28]1[CH:33]=[CH:32][C:31]([O:34][CH2:35][C:36]2[CH:41]=[CH:40][CH:39]=[C:38]([F:42])[CH:37]=2)=[C:30]([Cl:43])[CH:29]=1)=O)(C)(C)C>C(O)(C(F)(F)F)=O>[NH:8]1[CH2:13][CH2:12][O:11][CH2:10][C@@H:9]1[CH2:14][O:15][C:16](=[O:45])[NH:17][C:18]1[C:19]([CH3:44])=[C:20]2[N:25]([CH:26]=1)[N:24]=[CH:23][N:22]=[C:21]2[NH:27][C:28]1[CH:33]=[CH:32][C:31]([O:34][CH2:35][C:36]2[CH:41]=[CH:40][CH:39]=[C:38]([F:42])[CH:37]=2)=[C:30]([Cl:43])[CH:29]=1

Participants

3

Reactant 1

HCID 58649722HCID 58649722, compound

Product 1

HCID 58649720HCID 58649720, compoundYield 53.3%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of 4D (100 mg, 0.156 mmol) in TFA (1.2 ml) was stirred at rt for 5 min. The solution was concentrated in vacuo and the residue was purified by a Shimadzu auto prep HPLC, employing 30% to 100% 10 min gradient, 6 min 100% holding elution with 0.1%TFA in MeOH-water solvent system, 220 nM detection, 20 mL/min elution with a YMC ODS S5 20×100 mm column to give 4E (45 mg, 53%). Analytical HPLC retention time=2.93 min. (YMC S5 ODS column 4.6×50 mm, 10–90% aqueous methanol over 4 minutes containing 0.2% phosphoric acid, 4 mL/min, monitoring at 220 nm) and a LC/MS M++1=541.

Workup

  1. concentrationThe solution was concentrated in vacuo
  2. customthe residue was purified by a Shimadzu auto prep HPLC
  3. custom30% to 100% 10 min gradient, 6 min 100%
  4. washelution with 0.1%
  5. washTFA in MeOH-water solvent system, 220 nM detection, 20 mL/min elution with a YMC ODS

Sources & evidence

ORD record
ord-9c784a5efe18470a8e6273e38318be60
Source dataset
uspto-grants-2006_06
Patent number
US07064203B2

Reaction notes

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