Hydrochloric Acid → 1-[5-(3'-Chloro-2-fluoro-6-methoxy-biphenyl-3-ylmethyl)-pyridin-2-yl]-ethylamine dihydrochloride

HRID 1632081Notes

Reaction equation

HRID 1632081 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[C:13]([O:14][CH3:15])=[CH:12][CH:11]=[C:10]([CH2:16][C:17]3[CH:18]=[CH:19][C:20]([CH:23]([NH2:25])[CH3:24])=[N:21][CH:22]=3)[C:9]=2[F:26])[CH:5]=[CH:6][CH:7]=1.O1CCOCC1.[ClH:33]>C(OCC)C>[ClH:1].[ClH:33].[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[C:13]([O:14][CH3:15])=[CH:12][CH:11]=[C:10]([CH2:16][C:17]3[CH:18]=[CH:19][C:20]([CH:23]([NH2:25])[CH3:24])=[N:21][CH:22]=3)[C:9]=2[F:26])[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 580199871-[5-(3'-Chloro-2-fluoro-6-methoxy-biphenyl-3-ylmethyl)-pyridin-2-yl]-ethylamine

Product 1

HCID 689999201-[5-(3'-Chloro-2-fluoro-6-methoxy-biphenyl-3-ylmethyl)-pyridin-2-yl]-ethylamine dihydrochlorideYield 71%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

In an 8 mL vial equipped with a stir bar was placed 1-[5-(3′-Chloro-2-fluoro-6-methoxy-biphenyl-3-ylmethyl)-pyridin-2-yl]-ethylamine (P-606, 115 mg, 0.311 mmol), diethyl ether (3 mL), 1,4-dioxane (300 uL) and 2M HCl in diethyl ether (600 uL). The mixture was stirred at ambient temperature for 15 minutes, the solid was collected, washed with diethyl ether (3 mL) and dried to produce 98 mg of P-606-diHCl as a light tan solid in 71% yield.

Workup

  1. customIn an 8 mL vial equipped with a stir bar
  2. customthe solid was collected
  3. washwashed with diethyl ether (3 mL)
  4. customdried
  5. customto produce 98 mg of P-606-diHCl as a light tan solid in 71% yield

Sources & evidence

ORD record
ord-f49fd974c5a04702a2985e5fe501aeed
Source dataset
uspto-grants-2014_07
Patent number
US08791267B2

Reaction notes

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