HCID 86630517, compound → HCID 24751744, compound

HRID 1472217Notes

Reaction equation

HRID 1472217 reaction equation
C(OC([N:6]1[C:10]([NH:11][C:12](=[O:50])[C:13]2[CH:18]=[CH:17][C:16]([N:19]3[CH2:24][CH2:23][O:22][CH2:21][CH2:20]3)=[CH:15][C:14]=2[NH:25][C:26]([C@@H:28]2[CH2:32][CH2:31][CH2:30][N:29]2C(OCC2C3C=CC=CC=3C3C2=CC=CC=3)=O)=[O:27])=[C:9]2[CH:51](CC)[N:52]([S:56]([C:59]3[CH:64]=[C:63]([F:65])[CH:62]=[C:61]([F:66])[CH:60]=3)(=[O:58])=[O:57])[C:53]([CH3:55])([CH3:54])[C:8]2=[N:7]1)=O)C>CO.ClCCl.N1CCCCC1>[F:66][C:61]1[CH:60]=[C:59]([S:56]([N:52]2[CH2:51][C:9]3[C:10]([NH:11][C:12]([C:13]4[CH:18]=[CH:17][C:16]([N:19]5[CH2:24][CH2:23][O:22][CH2:21][CH2:20]5)=[CH:15][C:14]=4[NH:25][C:26]([C@@H:28]4[CH2:32][CH2:31][CH2:30][NH:29]4)=[O:27])=[O:50])=[N:6][NH:7][C:8]=3[C:53]2([CH3:55])[CH3:54])(=[O:58])=[O:57])[CH:64]=[C:63]([F:65])[CH:62]=1

Participants

5

Reactant 1

HCID 86630517HCID 86630517, compound

Product 1

HCID 24751744HCID 24751744, compoundYield 74.4%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 6344DichloromethaneSolventHCID 8082PiperidineSolvent

Procedure

To a solution of ethyl 5-(3,5-difluoro-benzenesulfonyl)-3-(2-{[(S)-1-(9H-fluoren-9-ylmethoxycarbonyl)-pyrrolidine-2-carbonyl]-amino}-4-morpholin-4-yl-benzoylamino)-6,6-dimethyl-5,6-dihydro-4H-pyrrolo[3,4-c]pyrazole-2-carboxylic acid ethyl ester (0.3 g, 0.32 mmol) in MeOH (10 mL) and dichloromethane (3 mL), piperidine (1 mL) was added and the reaction mixture stirred at room temperature for 12 hours. After evaporation to dryness, the residue was washed with petroleum ether and purified by flash chromatography on silica gel, using a mixture dichloromethane-MeOH 95:5 as the eluant, affording the title compound as pale yellow powder (0.15 g).

Workup

  1. customAfter evaporation to dryness
  2. washthe residue was washed with petroleum ether
  3. custompurified by flash chromatography on silica gel

Sources & evidence

ORD record
ord-63c6574045994ebcbcea1f5b042c7606
Source dataset
uspto-grants-2015_04
Patent number
US09012487B2

Reaction notes

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