HCID 86614401, compound → HCID 86614400, compound

HRID 1673326Notes

Reaction equation

HRID 1673326 reaction equation
C(OC([N:11]1[CH2:16][CH2:15][N:14]([C:17]([C:19]([NH:22][C:23]([CH2:25]/[CH:26]=[CH:27]/[C:28]2[CH:33]=[CH:32][C:31]([C:34]#[C:35][C:36]3[CH:44]=[CH:43][CH:42]=[C:41]4[C:37]=3[C:38]([O:45][C@@H:46]3[O:72][C@H:71]([CH2:73][O:74][C:75](=[O:80])[C:76]([CH3:79])([CH3:78])[CH3:77])[C@@H:63]([O:64][C:65](=[O:70])[C:66]([CH3:69])([CH3:68])[CH3:67])[C@H:55]([O:56][C:57](=[O:62])[C:58]([CH3:61])([CH3:60])[CH3:59])[C@H:47]3[O:48][C:49](=[O:54])[C:50]([CH3:53])([CH3:52])[CH3:51])=[N:39][NH:40]4)=[CH:30][CH:29]=2)=[O:24])([CH3:21])[CH3:20])=[O:18])[CH2:13][CH2:12]1)=O)C1C=CC=CC=1>CO.[C].[Pd]>[N:14]1([C:17]([C:19]([NH:22][C:23]([CH2:25][CH2:26][CH2:27][C:28]2[CH:29]=[CH:30][C:31]([CH2:34][CH2:35][C:36]3[CH:44]=[CH:43][CH:42]=[C:41]4[C:37]=3[C:38]([O:45][C@@H:46]3[O:72][C@H:71]([CH2:73][O:74][C:75](=[O:80])[C:76]([CH3:79])([CH3:78])[CH3:77])[C@@H:63]([O:64][C:65](=[O:70])[C:66]([CH3:69])([CH3:68])[CH3:67])[C@H:55]([O:56][C:57](=[O:62])[C:58]([CH3:59])([CH3:60])[CH3:61])[C@H:47]3[O:48][C:49](=[O:54])[C:50]([CH3:51])([CH3:52])[CH3:53])=[N:39][NH:40]4)=[CH:32][CH:33]=2)=[O:24])([CH3:21])[CH3:20])=[O:18])[CH2:15][CH2:16][NH:11][CH2:12][CH2:13]1

Participants

4

Reactant 1

HCID 86614401HCID 86614401, compound

Product 1

HCID 86614400HCID 86614400, compoundYield 99.8%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolvent

Procedure

To a solution of 4-[2-(4-{(E)-3-[1-{[4-(benzyloxy-carbonyl)piperazin-1-yl]carbonyl}-1-(methyl)ethyl-carbamoyl]prop-1-enyl}phenyl)ethynyl]-3-(2,3,4,6-tetra-O-pivaloyl-β-D-glucopyranosyloxy)-1H-indazole (34 mg) in methanol (3 mL) was added 10% palladium-carbon powder (10 mg), and the mixture was stirred at room temperature under a hydrogen atmosphere for 2 hours. The insoluble material was removed by filtration, and the solvent of the filtrate was removed under reduced pressure to give 4-{2-[4-(3-{1-[(piperazin-1-yl)-carbonyl]-1-(methyl)ethylcarbamoyl}propyl)phenyl]ethyl}-3-(2,3,4,6-tetra-O-pivaloyl-β-D-glucopyranosyloxy)-1H-indazole (30 mg). This material was dissolved in methanol (3 mL). To the solution was added lithium hydroxide monohydrate (6 mg), and the mixture was stirred at room temperature overnight. To the reaction mixture was added acetic acid (0.1 mL), and the resulting mixture was concentrated under reduced pressure. The residue was purified by solid phase extraction on ODS (washing solvent: distilled water, eluent: methanol) to give the title compound (17 mg).

Workup

  1. customThe insoluble material was removed by filtration
  2. customthe solvent of the filtrate was removed under reduced pressure

Sources & evidence

ORD record
ord-45cd6f292e4648fd8c56b26744051231
Source dataset
uspto-grants-2011_08
Patent number
US07998975B2

Reaction notes

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