Hydrochloric Acid → HCID 72547957, compound

HRID 1057042Notes

Reaction equation

HRID 1057042 reaction equation
[OH:1][CH2:2][CH2:3][N:4]([CH3:32])[C:5]1[CH:10]=[C:9]([CH:11]2[CH2:16][CH2:15][N:14](C(OC(C)(C)C)=O)[CH2:13][CH2:12]2)[CH:8]=[C:7]([NH:24][C:25]2[CH:30]=[C:29]([CH3:31])[CH:28]=[CH:27][N:26]=2)[N:6]=1.Cl.O1CCOCC1>C(Cl)Cl>[CH3:32][N:4]([C:5]1[CH:10]=[C:9]([CH:11]2[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]2)[CH:8]=[C:7]([NH:24][C:25]2[CH:30]=[C:29]([CH3:31])[CH:28]=[CH:27][N:26]=2)[N:6]=1)[CH2:3][CH2:2][OH:1]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 90067631HCID 90067631, compound

Product 1

HCID 72547957HCID 72547957, compoundYield 49.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl 4-(2-((2-hydroxyethyl)(methyl)amino)-6-(4-methylpyridin-2-ylamino)pyridin-4-yl)piperidine-1-carboxylate (100 mg, 0.22 mmol) in DCM (1.0 mL) was added hydrogen chloride (4 mol/L) in 1,4-dioxane (3.0 mL, 12 mmol). The resultant was stirred at room temperature for 3 h. It was purified by HPLC to give 37 mg (48%) of the title compound as a light yellow solid. 1H NMR (400 MHz, DMSO) δ 9.00 (s, 1H), 8.02 (d, J=5.1 Hz, 1H), 7.95 (s, 1H), 6.64 (d, J=5.1 Hz, 1H), 6.42 (s, 1H), 5.90 (s, 1H), 4.64 (s, 1H), 3.64-3.53 (m, 4H), 3.05-2.95 (m, 5H), 2.58-2.52 (m, 1H), 2.50-2.31 (m, 3H), 2.25 (s, 3H), 1.69-1.58 (m, 2H), 1.55-1.40 (m, 2H). LC-MS: m/z=342 (M+H+).

Workup

  1. customIt was purified by HPLC

Sources & evidence

ORD record
ord-35297e5587884e188c1169a2ab946dcc
Source dataset
uspto-grants-2016_07
Patent number
US09399636B2

Reaction notes

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