Hydrochloric Acid → HCID 67508395, compound

HRID 2172881Notes

Reaction equation

HRID 2172881 reaction equation
[Cl:1][C:2]1[C:3]([C:22]2[C:27]([CH3:28])=[CH:26][C:25]([CH3:29])=[CH:24][N:23]=2)=[N:4][C:5]([N:8]2[CH2:13][CH2:12][CH:11]([NH:14]C(=O)OC(C)(C)C)[CH2:10][CH2:9]2)=[CH:6][CH:7]=1.Cl>CO>[Cl:1][C:2]1[C:3]([C:22]2[C:27]([CH3:28])=[CH:26][C:25]([CH3:29])=[CH:24][N:23]=2)=[N:4][C:5]([N:8]2[CH2:13][CH2:12][CH:11]([NH2:14])[CH2:10][CH2:9]2)=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 86691909HCID 86691909, compound

Product 1

HCID 67508395HCID 67508395, compoundYield 144.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a suspension of tert-butyl [1-(3-chloro-3′,5′-dimethyl-2,2′-bipyridin-6-yl)piperidin-4-yl]carbamate (220 mg, 0.528 mmol) in MeOH (5.28 mL) was added HCl (2.64 mL, 4M in dioxane, 2.64 mmol). The resulting yellow solution was stirred at rt for 4 h and concentrated to get 242 mg (99%) of the title compound as a yellow solid. m/z (APCI+) for C17H21N4Cl 317.20 (M+H)+. 1H NMR (400 MHz, DMSO-d6) δ ppm 8.65 (s, 1H) 8.30 (br. s., 3 H) 8.28 (br. s., 1 H) 7.84 (d, J=9.09 Hz, 1 H) 7.14 (d, J=9.35 Hz, 1 H) 4.29 (d, J=13.39 Hz, 2 H) 3.22-3.34 (m, 1 H) 2.95 (t, J=12.25 Hz, 2 H) 2.48 (s, 3 H) 2.24 (s, 3 H) 1.96 (d, J=10.86 Hz, 2 H) 1.48-1.60 (m, 2 H).

Workup

  1. concentrationconcentrated

Sources & evidence

ORD record
ord-85facd8f6fb44285a758c2ae2f5d0f34
Source dataset
uspto-grants-2015_06
Patent number
US09056865B2

Reaction notes

Loading…