Hydrochloric Acid → HCID 178484277, compound

HRID 526763Notes

Reaction equation

HRID 526763 reaction equation
[CH:1]([C:4]1[CH:5]=[C:6]([C:13]2[C:17]([CH2:18][N:19]([CH3:31])[CH2:20][CH2:21][N:22](C)[C:23](=O)OC(C)(C)C)=[CH:16][N:15](C3CCCCO3)[N:14]=2)[CH:7]=[C:8]([CH:10]([CH3:12])[CH3:11])[CH:9]=1)([CH3:3])[CH3:2].Cl>O1CCOCC1>[CH3:3][CH:1]([C:4]1[CH:5]=[C:6]([C:13]2[C:17]([CH2:18][N:19]([CH3:31])[CH2:20][CH2:21][NH:22][CH3:23])=[CH:16][NH:15][N:14]=2)[CH:7]=[C:8]([CH:10]([CH3:11])[CH3:12])[CH:9]=1)[CH3:2]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 117665899tert-butyl N-[2-[([3-(3,5-diisopropylphenyl)-1-(oxan-2-yl)-1H-pyrazol-4-yl]methyl)(methyl)amino]ethyl]-N-methylcarbamate

Product 1

HCID 178484277HCID 178484277, compoundYield 113.1%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A solution of tert-butyl N-[2-[([3-(3,5-diisopropylphenyl)-1-(oxan-2-yl)-1H-pyrazol-4-yl]methyl)(methyl)amino]ethyl]-N-methylcarbamate (180 mg, 0.35 mmol, 1.00 equiv) in a saturated hydrogen chloride solution in 1,4-dioxane (5 mL) was stirred at room temperature overnight. The resulting mixture was concentrated under vacuum and the residue was triturated with 1×50 mL of ether to give 130 mg (92%) of ([3-[3,5-bis(propan-2-yl)phenyl]-1H-pyrazol-4-yl]methyl)(methyl)[2-(methylamino)ethyl]amine as a light yellow solid. 1H NMR (300 MHz, CD3OD): δ 8.25-8.22 (m, 1H), 7.31 (s, 1H), 7.27 (s, 2H), 4.70-4.37 (m, 2H), 3.60-3.35 (m, 4H), 3.04-2.94 (m, 2H), 2.72 (s, 3H), 2.71 (s, 3H), 1.31 (d, J=7.2 Hz, 12H) ppm. LCMS (method H, ESI): RT=1.34 min, m/z=329.1 [M+H]+.

Workup

  1. concentrationThe resulting mixture was concentrated under vacuum
  2. customthe residue was triturated with 1×50 mL of ether

Sources & evidence

ORD record
ord-1cfe5889c883435791f68cc79fff5dd2
Source dataset
uspto-grants-2016_05
Patent number
US09346761B2

Reaction notes

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