Hydrogen chloride-ethyl acetate → HCID 66906426, compound

HRID 1691726Notes

Reaction equation

HRID 1691726 reaction equation
C(OC([N:8]([CH2:21][CH:22]1[CH2:27][CH2:26][N:25]([C:28]2[C:36]([Cl:37])=[CH:35][C:31]([C:32]([OH:34])=[O:33])=[CH:30][N:29]=2)[CH2:24][CH:23]1[C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][C:39]=1[F:44])[C@@H:9]([C:11]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH:14]=[CH:13][CH:12]=1)[CH3:10])=O)(C)(C)C.Cl.C(OCC)(=O)C>C(OCC)(=O)C>[ClH:37].[Cl:37][C:36]1[C:28]([N:25]2[CH2:26][CH2:27][CH:22]([CH2:21][NH:8][C@@H:9]([C:11]3[C:20]4[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=4)[CH:14]=[CH:13][CH:12]=3)[CH3:10])[CH:23]([C:38]3[CH:43]=[CH:42][CH:41]=[CH:40][C:39]=3[F:44])[CH2:24]2)=[N:29][CH:30]=[C:31]([CH:35]=1)[C:32]([OH:34])=[O:33]

Participants

4

Reactant 2

HCID 21866389Hydrogen chloride-ethyl acetateHCID 66906542HCID 66906542, compound

Product 1

HCID 66906426HCID 66906426, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of the crude 6-[4-({(tert-butoxycarbonyl)[(1R)-1-(1-naphthyl)ethyl]amino}methyl)-3-(2-fluorophenyl)piperidin-1-yl]-5-chloronicotinic acid obtained in the aforementioned reaction in 2.0 mL of ethyl acetate was added 1.00 mL of a 4 M hydrogen chloride/ethyl acetate solution, followed by stirring at room temperature for 2 hours. The reaction mixture was concentrated under reduced pressure, and the residue was purified by reverse phase silica gel column chromatography (acetonitrile-0.01 M hydrochloric acid) to obtain 56 mg of 5-chloro-6-[3-(2-fluorophenyl)-4-({[(1R)-1-(1-naphthyl)ethyl]amino}methyl)piperidin-1-yl]nicotinic acid hydrochloride as a white solid.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customthe residue was purified by reverse phase silica gel column chromatography (acetonitrile-0.01 M hydrochloric acid)

Sources & evidence

ORD record
ord-a1ba808e37084a708fa4f18756c8a81f
Source dataset
uspto-grants-2012_04
Patent number
US08153658B2

Reaction notes

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