Methanol → 1-(5'-Chloro-3'-fluoro-3,5-dimethyl-2,4'-bipyridin-2'-yl)piperidin-4-amine

HRID 2172884Notes

Reaction equation

HRID 2172884 reaction equation
[Cl:1][C:2]1[C:3]([C:23]2[C:28]([CH3:29])=[CH:27][C:26]([CH3:30])=[CH:25][N:24]=2)=[C:4]([F:22])[C:5]([N:8]2[CH2:13][CH2:12][CH:11]([NH:14]C(=O)OC(C)(C)C)[CH2:10][CH2:9]2)=[N:6][CH:7]=1.O1CCOCC1.CO>Cl>[Cl:1][C:2]1[C:3]([C:23]2[C:28]([CH3:29])=[CH:27][C:26]([CH3:30])=[CH:25][N:24]=2)=[C:4]([F:22])[C:5]([N:8]2[CH2:9][CH2:10][CH:11]([NH2:14])[CH2:12][CH2:13]2)=[N:6][CH:7]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 312751,4-DioxaneHCID 86691910Tert-butyl 1-(5'-chloro-3'-fluoro-3,5-dimethyl-2,4'-bipyridin-2'-yl)piperidin-4-ylcarbamate

Product 1

HCID 690435731-(5'-Chloro-3'-fluoro-3,5-dimethyl-2,4'-bipyridin-2'-yl)piperidin-4-amineYield 121.7%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A solution of tert-butyl (1-(5′-chloro-3′-fluoro-3,5-dimethyl-[2,4′-bipyridin]-2′-yl)piperidin-4-yl)carbamate (160 mg, 0.368 mmol) in 4 M HCl in dioxane (3.0 mL, 12.0 mmol) and MeOH (1.0 mL) was stirred at rt for 2 h. After concentration, the residue was further dried under vacuum to give 150 mg (100%) of pale yellow solid as a di-HCl salt: LRMS (M+H)+: 335.0; 1H NMR (400 MHz, DMSO-d6) δ 1.50-1.72 (m, 2 H), 1.94-2.03 (m, 2 H), 2.10 (s, 3 H), 2.37 (s, 3 H), 2.89-3.12 (m, 2 H), 3.20-3.33 (m, 1 H), 3.92-4.08 (m, 2 H), 6.62 (br. s., 1 H), 7.77 (s, 1 H), 8.12-8.31 (m, 4 H), 8.44 (s, 1 H).

Workup

  1. concentrationAfter concentration
  2. customthe residue was further dried under vacuum

Sources & evidence

ORD record
ord-9ce37c5362a144ed838041830bd4b1c8
Source dataset
uspto-grants-2015_06
Patent number
US09056865B2

Reaction notes

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