HCID 67050611, compound → HCID 58203868, compound

HRID 1849407Notes

Reaction equation

HRID 1849407 reaction equation
[CH:1]([N:4]1[C:8]([C:9]2[S:10][C:11]3[CH2:12][CH2:13][O:14][C:15]4[CH:22]=[C:21]([C:23]5[CH:24]=[N:25][N:26]([CH2:28][CH2:29][O:30][P:31](=[O:48])([O:40]CC6C=CC=CC=6)[O:32]CC6C=CC=CC=6)[CH:27]=5)[CH:20]=[CH:19][C:16]=4[C:17]=3[N:18]=2)=[N:7][CH:6]=[N:5]1)([CH3:3])[CH3:2]>CO.CCOC(C)=O>[CH:1]([N:4]1[C:8]([C:9]2[S:10][C:11]3[CH2:12][CH2:13][O:14][C:15]4[CH:22]=[C:21]([C:23]5[CH:24]=[N:25][N:26]([CH2:28][CH2:29][O:30][P:31](=[O:32])([OH:40])[OH:48])[CH:27]=5)[CH:20]=[CH:19][C:16]=4[C:17]=3[N:18]=2)=[N:7][CH:6]=[N:5]1)([CH3:3])[CH3:2]

Participants

3

Reactant 1

HCID 67050611HCID 67050611, compound

Product 1

HCID 58203868HCID 58203868, compound

Reagents, catalysts & solvents 1

HCID 21584119Ethylacetate methanolSolvent

Procedure

Phosphoric acid dibenzyl ester 2-{4-[2-(2-isopropyl-2H-[1,2,4]triazol-3-yl)-4,5-dihydro-6-oxa-3-thia-1-aza-benzo[e]azulen-8-yl]-pyrazol-1-yl}-ethyl ester (180 mg, 0.26 mmol) was dissolved in methanol:EtOAc (1:1, 6 mL) and the solution was flushed with bubbling nitrogen. Palladium hydroxide (5% on carbon, 40 mg) was added and the reaction mixture was placed under hydrogen atmosphere (1 atm, balloon) overnight while rapidly stirred. Filtration over celite and concentration of the filtrate gave 482. Lyophilization of a solution in acetonitrile and 1% NH4OH in water gave 482 as the bis-ammonium salt.

Workup

  1. customthe solution was flushed with bubbling nitrogen
  2. additionPalladium hydroxide (5% on carbon, 40 mg) was added
  3. custom(1 atm, balloon) overnight
  4. filtrationFiltration over celite and concentration of the filtrate

Sources & evidence

ORD record
ord-9be69dde9206429ead984267a2fed494
Source dataset
uspto-grants-2015_02
Patent number
US08952043B2

Reaction notes

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