Hydrochloric Acid → HCID 118251454, compound

HRID 2283460Notes

Reaction equation

HRID 2283460 reaction equation
[ClH:1].C[O:3][C:4]1[N:9]=[CH:8][C:7]([C:10]2[CH:15]=[CH:14][N:13]=[CH:12][CH:11]=2)=[CH:6][C:5]=1[NH:16][C@@H:17]1[CH2:22][CH2:21][CH2:20][N:19](C(OC(C)(C)C)=O)[CH2:18]1>O1CCOCC1.C(O)C>[ClH:1].[NH:19]1[CH2:20][CH2:21][CH2:22][C@@H:17]([NH:16][C:5]2[C:4](=[O:3])[NH:9][CH:8]=[C:7]([C:10]3[CH:15]=[CH:14][N:13]=[CH:12][CH:11]=3)[CH:6]=2)[CH2:18]1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 118251098HCID 118251098, compound

Product 1

HCID 118251454HCID 118251454, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
80 °C

Procedure

A solution of HCl in dioxane (20 mL) was added to (R)-tert-butyl 3-((6-methoxy-[3,4′-bipyridin]-5-yl)amino)piperidine-1-carboxylate (1.00 g, 2.60 mmol) in ethanol (10 mL). The mixture was heated at 80° C. for 12 h in a sealed tube. After cooling to room temperature the mixture was concentrated and the crude residue was triturated with diethyl ether to afford 0.60 g of the desired compound: 1H NMR (300 MHz, DMSO-d6) 12.29 (br s, 1H), 9.30-9.50 (m, 1H), 8.90-9.10 (m, 1H), 8.76 (br s 2H), 8.32 (br s, 2H), 7.74 (s, 1H), 7.04 (s, 1H), 5.65-5.90 (m, 1H), 3.20-4.10 (m, 5H), 2.60-2.90 (m, 1H), 1.60-2.05 (m, 3H); MS (ES) m/z 271 (M+H).

Workup

  1. temperatureAfter cooling to room temperature the mixture
  2. concentrationwas concentrated
  3. customthe crude residue was triturated with diethyl ether

Sources & evidence

ORD record
ord-03cb941cacc348d4864fa4cc7a527f10
Source dataset
uspto-grants-2015_09
Patent number
US09145393B2

Reaction notes

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