Hydrochloric Acid → 1',2',3',4',5',6'-Hexahydro-[2,4']bipyridinyl-6-carboxylic acid methyl-(1,2,3,4-tetrahydro-naphthalen-1-yl)-amide hydrochloride salt

HRID 385300Notes

Reaction equation

HRID 385300 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([C:20](=[O:33])[N:21]([CH3:32])[CH:22]3[C:31]4[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=4)[CH2:25][CH2:24][CH2:23]3)[N:15]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.[ClH:34].O1CCOCC1>>[ClH:34].[CH3:32][N:21]([CH:22]1[C:31]2[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=2)[CH2:25][CH2:24][CH2:23]1)[C:20]([C:16]1[N:15]=[C:14]([CH:11]2[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]2)[CH:19]=[CH:18][CH:17]=1)=[O:33]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 66686878tert-Butyl 4-{6-[methyl(1,2,3,4-tetrahydronaphthalen-1-yl)carbamoyl]pyridin-2-yl}-piperidine-1-carboxylate

Product 1

HCID 669731291',2',3',4',5',6'-Hexahydro-[2,4']bipyridinyl-6-carboxylic acid methyl-(1,2,3,4-tetrahydro-naphthalen-1-yl)-amide hydrochloride saltYield 93%

Procedure

To a solution of 6-[methyl-(1,2,3,4-tetrahydro-naphthalen-1-yl)-carbamoyl]-3′,4′,5′,6′-tetrahydro-2′H-[2,4′]bipyridinyl-1′-carboxylic acid tert-butyl ester (202 mg, 0.45 mmol) was added a solution of 4M HCl in dioxane (1.13 mL, 4.5 mmol)) at RT. After stirring overnight at RT, the solvent was evaporated under reduce pressure to give 1′,2′,3′,4′,5′,6′-hexahydro-[2,4′]bipyridinyl-6-carboxylic acid methyl-(1,2,3,4-tetrahydro-naphthalen-1-yl)-amide hydrochloride salt (162 mg, 93%). 1H-NMR (400 MHz, d6-DMSO): δ=1.83-2.02 (m, 6H), 2.51 (s, 3H), 2.52-2.59 (m, 2H), 2.71-3.03 (m, 2H), 3.29-3.38 (m, 2H), 3.97-4.05 (m, 2H), 4.78-4.83 (m, 1H), 7.08-7.23 (m, 4H), 7.36-7.41 (m, 1H), 7.52-7.55 (m, 1H), 7.90-7.95 (m, 1H), 8.81 (br, 1H), 9.04 (br, 1H).

Workup

  1. customthe solvent was evaporated

Sources & evidence

ORD record
ord-ada08d0768454a5c8808b57d21467e00
Source dataset
uspto-grants-2013_02
Patent number
US08367844B2

Reaction notes

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