Hydrochloric Acid → CNV1014802 (hydrochloride)

HRID 410004Notes

Reaction equation

HRID 410004 reaction equation
[F:1][C:2]1[CH:23]=[CH:22][CH:21]=[CH:20][C:3]=1[CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([C@@H:12]2[NH:16][C@H:15]([C:17]([NH2:19])=[O:18])[CH2:14][CH2:13]2)=[CH:8][CH:7]=1.[ClH:24].O1CCOCC1>C(OCC)(=O)C.CO>[ClH:24].[F:1][C:2]1[CH:23]=[CH:22][CH:21]=[CH:20][C:3]=1[CH2:4][O:5][C:6]1[CH:7]=[CH:8][C:9]([C@@H:12]2[NH:16][C@H:15]([C:17]([NH2:19])=[O:18])[CH2:14][CH2:13]2)=[CH:10][CH:11]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 16046068Raxatrigine

Product 1

HCID 16046067CNV1014802 (hydrochloride)Yield 93%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of E1 (72 mg, 0.23 mmol) in a mixture of ethyl acetate (1.0 ml) and methanol (1.0 ml) was added 4M HCl in 1,4-dioxane (57.5 uL, 0.23 mmol) at 0° C. The mixture was stirred for 1.5 h and slowly allowed to warm to room temperature. After evaporating the solvent, the residue was triturated with diethyl ether to afford the title compound as a white solid (75 mg, 93% yield).

Workup

  1. customAfter evaporating the solvent
  2. customthe residue was triturated with diethyl ether

Sources & evidence

ORD record
ord-9d79159944334f11a640c50710ba6da4
Source dataset
uspto-grants-2014_06
Patent number
US08759542B2

Reaction notes

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