HCID 58149882, compound → HCID 44476675, compound

HRID 2192535Notes

Reaction equation

HRID 2192535 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:12]2[O:16][N:15]=[C:14]([C:17]3[CH:26]=[CH:25][CH:24]=[C:23]4[C:18]=3[CH:19]=[CH:20][N:21]=[C:22]4[CH2:27][CH2:28][C:29]([O:31]C(C)(C)C)=[O:30])[N:13]=2)[CH:5]=[N:6][C:7]=1[O:8][CH:9]([CH3:11])[CH3:10]>Cl.O1CCOCC1.CN1C(=O)CCC1>[Cl:1][C:2]1[CH:3]=[C:4]([C:12]2[O:16][N:15]=[C:14]([C:17]3[CH:26]=[CH:25][CH:24]=[C:23]4[C:18]=3[CH:19]=[CH:20][N:21]=[C:22]4[CH2:27][CH2:28][C:29]([OH:31])=[O:30])[N:13]=2)[CH:5]=[N:6][C:7]=1[O:8][CH:9]([CH3:10])[CH3:11]

Participants

5

Reactant 1

HCID 58149882HCID 58149882, compound

Product 1

HCID 44476675HCID 44476675, compoundYield 4.5%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 13387N-methyl-2-pyrrolidoneSolventHCID 312751,4-DioxaneSolvent

Procedure

1,1-Dimethylethyl 3-[5-(5-{5-chloro-6-[(1-methylethyl)oxy]-3-pyridinyl}-1,2,4-oxadiazol-3-yl)-1-isoquinolinyl]propanoate (D53; 54 mg, 0.111 mmol) was dissolved in 4M hydrogen chloride in 1,4-dioxane (10 ml) and the mixture allowed to stand at room temperature for 2 h. The solvent was evaporated in vacuo to give a colourless gum which was triturated under dry ether (5 ml) to give a white solid which was dissolved in NMP (0.5 ml) and purified by Mass Directed Preparative HPLC (Supelcosil ABZ+Plus column, eluting with solvents A/B (A: Water+0.1% Formic acid, B: MeCN:Water 95:5+0.05% Formic acid)). The solvent was evaporated in vacuo to give the title compound (2.2 mg)

Workup

  1. customThe solvent was evaporated in vacuo
  2. customto give a colourless gum which
  3. customwas triturated under dry ether (5 ml)
  4. customto give a white solid which
  5. custompurified by Mass Directed Preparative HPLC (Supelcosil ABZ+Plus column
  6. washeluting with solvents A/B (A: Water+0.1% Formic acid, B
  7. customThe solvent was evaporated in vacuo

Sources & evidence

ORD record
ord-6d0c922b832a471db417ff95154d39f5
Source dataset
uspto-grants-2012_12
Patent number
US08329730B2

Reaction notes

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