Hydrochloric Acid → HCID 59515859, compound

HRID 1161195Notes

Reaction equation

HRID 1161195 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([NH:11][C:12]2[CH:21]=[CH:20][CH:19]=[C:18]3[C:13]=2[CH:14]=[CH:15][N:16]([CH2:23][C@@H:24]2[CH2:28][CH2:27][CH2:26][N:25]2C(OC(C)(C)C)=O)[C:17]3=[O:22])=[O:10])=[CH:4][C:3]=1[C:36]([F:39])([F:38])[F:37].O1CCOCC1.Cl>CCOCC>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([NH:11][C:12]2[CH:21]=[CH:20][CH:19]=[C:18]3[C:13]=2[CH:14]=[CH:15][N:16]([CH2:23][C@@H:24]2[CH2:28][CH2:27][CH2:26][NH:25]2)[C:17]3=[O:22])=[O:10])=[CH:4][C:3]=1[C:36]([F:39])([F:37])[F:38]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 59515797HCID 59515797, compound

Product 1

HCID 59515859HCID 59515859, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Into a 20 ml reaction vessel was combined (S)-tert-butyl 2-((5-(2-(4-chloro-3-(trifluoromethyl)phenyl)acetamido)-1-oxoisoquinolin-2(1H)-yl)methyl)pyrrolidine-1-carboxylate (20.0 mg, 0.0000355 mol) and 1,4-dioxane (5 mL, 0.06 mol). Hydrogen chloride (0.016 g, 0.00044 mol) as a 2.0M solution in ether was added dropwise. The reaction was allowed to stir overnight. A white preciptate had formed and was filtered, washed with ether, and dried. The product was dissolved in diethylamine and DMSO (1 mL) and was purified by HPLC using a Phenomenex AXIA packed C18 column (100×21.2 10 micron) at pH 10. The combined pure fractions were reduced in vacuo to yield the title compound as a white solid. LC/MS M+H=464.2.

Workup

  1. customInto a 20 ml reaction vessel
  2. customA white preciptate had formed
  3. filtrationwas filtered
  4. washwashed with ether
  5. customdried
  6. dissolutionThe product was dissolved in diethylamine
  7. customDMSO (1 mL) and was purified by HPLC

Sources & evidence

ORD record
ord-b4bf4ea7614b4b098334f460c7754b75
Source dataset
uspto-grants-2010_10
Patent number
US07816371B2

Reaction notes

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