HCID 54277563, compound → HCID 44265290, compound

HRID 651649Notes

Reaction equation

HRID 651649 reaction equation
Cl[C:2]1[C:7]2[CH:8]=[C:9]([CH2:11][N:12]3[CH2:16][CH2:15][C@H:14]([NH:17][S:18]([C:21]4[S:25][C:24]5[CH:26]=[C:27]([Cl:30])[CH:28]=[CH:29][C:23]=5[CH:22]=4)(=[O:20])=[O:19])[C:13]3=[O:31])[NH:10][C:6]=2[CH:5]=[CH:4][N:3]=1>[Pd].C(O)C>[O:31]=[C:13]1[C@@H:14]([NH:17][S:18]([C:21]2[S:25][C:24]3[CH:26]=[C:27]([Cl:30])[CH:28]=[CH:29][C:23]=3[CH:22]=2)(=[O:19])=[O:20])[CH2:15][CH2:16][N:12]1[CH2:11][C:9]1[NH:10][C:6]2[CH:5]=[CH:4][N:3]=[CH:2][C:7]=2[CH:8]=1

Participants

4

Reactant 1

HCID 54277563HCID 54277563, compound

Product 1

HCID 44265290HCID 44265290, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Conditions

Temperature
65 °C

Procedure

Palladium on carbon (0.01 g) is added to a solution of 6-chloro-benzo[b]thiophene-2-sulfonic acid [1-(4-chloro-1H-pyrrolo[3,2-c]pyridin-2-ylmethyl)-2-oxopyrrolidin-3-(S)-yl]-amide in 95% ethanol (5 mL) and charged with H2 gas. The mixture is heated at 65° C. overnight then cooled to room temperature and filtered through Celite. The solvent is removed and the crude product is purified by RP-HPLC eluting with a gradient of 10% CH3CN/H2O (0.1% TFA) to 100% CH3CN. The appropriate product fractions are lyophilized to give the title compound as a white solid.

Workup

  1. additioncharged with H2 gas
  2. temperaturethen cooled to room temperature
  3. filtrationfiltered through Celite
  4. customThe solvent is removed
  5. customthe crude product is purified by RP-HPLC
  6. washeluting with a gradient of 10% CH3CN/H2O (0.1% TFA) to 100% CH3CN

Sources & evidence

ORD record
ord-1c6cca9132ca48918e0d4b1aecb88115
Source dataset
uspto-grants-2001_08
Patent number
US06281227B1

Reaction notes

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