HCID 86602033, compound → 4-[(4-(3-[2-(Carbamoyl)ethylamino]propoxy)-2-methylphenyl)methyl]-5-isopropyl-3-(2,3,4,6-tetra-O-pivaloyl-beta-D-glucopyranosyloxy)-1H-pyrazole

HRID 1869029Notes

Reaction equation

HRID 1869029 reaction equation
C([N:8]([CH2:14][CH2:15][CH2:16][O:17][C:18]1[CH:23]=[CH:22][C:21]([CH2:24][C:25]2[C:26]([O:33][C@@H:34]3[O:60][C@H:59]([CH2:61][O:62][C:63](=[O:68])[C:64]([CH3:67])([CH3:66])[CH3:65])[C@@H:51]([O:52][C:53](=[O:58])[C:54]([CH3:57])([CH3:56])[CH3:55])[C@H:43]([O:44][C:45](=[O:50])[C:46]([CH3:49])([CH3:48])[CH3:47])[C@H:35]3[O:36][C:37](=[O:42])[C:38]([CH3:41])([CH3:40])[CH3:39])=[N:27][NH:28][C:29]=2[CH:30]([CH3:32])[CH3:31])=[C:20]([CH3:69])[CH:19]=1)[CH2:9][CH2:10][C:11](=[O:13])[NH2:12])C1C=CC=CC=1>O1CCCC1.[C].[Pd]>[C:11]([CH2:10][CH2:9][NH:8][CH2:14][CH2:15][CH2:16][O:17][C:18]1[CH:23]=[CH:22][C:21]([CH2:24][C:25]2[C:26]([O:33][C@@H:34]3[O:60][C@H:59]([CH2:61][O:62][C:63](=[O:68])[C:64]([CH3:67])([CH3:66])[CH3:65])[C@@H:51]([O:52][C:53](=[O:58])[C:54]([CH3:56])([CH3:55])[CH3:57])[C@H:43]([O:44][C:45](=[O:50])[C:46]([CH3:47])([CH3:48])[CH3:49])[C@H:35]3[O:36][C:37](=[O:42])[C:38]([CH3:39])([CH3:40])[CH3:41])=[N:27][NH:28][C:29]=2[CH:30]([CH3:31])[CH3:32])=[C:20]([CH3:69])[CH:19]=1)(=[O:13])[NH2:12]

Participants

4

Reactant 1

HCID 86602033HCID 86602033, compound

Product 1

HCID 689419094-[(4-(3-[2-(Carbamoyl)ethylamino]propoxy)-2-methylphenyl)methyl]-5-isopropyl-3-(2,3,4,6-tetra-O-pivaloyl-beta-D-glucopyranosyloxy)-1H-pyrazoleYield 100%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-[(4-{3-[N-benzyl-N-(2-carbamoylethyl)amino]propoxy}-2-methylphenyl)methyl]-5-isopropyl-3-(2,3,4,6-tetra-O-pivaloyl-β-D-glucopyranosyloxy)-1H-pyrazole (0.96 g) in tetrahydrofuran (5 mL) was added 10% palladium-carbon powder (0.1 g), and the mixture was stirred at room temperature under a hydrogen atmosphere overnight. The insoluble material was removed by filtration, and the filtrate was concentrated under reduced pressure to give the title compound (0.87 g).

Workup

  1. customThe insoluble material was removed by filtration
  2. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-0a879635a0ab41cf8050343d2b422d95
Source dataset
uspto-grants-2009_12
Patent number
US07635684B2

Reaction notes

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