tert-butyl methyl(2-(methyl((3-(3-(3-methylbut-2-enamido)phenyl)-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazol-4-yl)methyl)amino)ethyl)carbamate → 3-methyl-N-(3-(4-((methyl(2-(methylamino)ethyl)amino)methyl)-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazol-3-yl)phenyl)but-2-enamide

HRID 570787Notes

Reaction equation

HRID 570787 reaction equation
[CH3:1][N:2]([CH2:10][CH2:11][N:12]([CH3:38])[CH2:13][C:14]1[C:15]([C:25]2[CH:30]=[CH:29][CH:28]=[C:27]([NH:31][C:32](=[O:37])[CH:33]=[C:34]([CH3:36])[CH3:35])[CH:26]=2)=[N:16][N:17]([CH:19]2[CH2:24][CH2:23][CH2:22][CH2:21][O:20]2)[CH:18]=1)C(=O)OC(C)(C)C>Cl>[CH3:35][C:34]([CH3:36])=[CH:33][C:32]([NH:31][C:27]1[CH:28]=[CH:29][CH:30]=[C:25]([C:15]2[C:14]([CH2:13][N:12]([CH3:38])[CH2:11][CH2:10][NH:2][CH3:1])=[CH:18][N:17]([CH:19]3[CH2:24][CH2:23][CH2:22][CH2:21][O:20]3)[N:16]=2)[CH:26]=1)=[O:37]

Participants

3

Reactant 1

HCID 117617465tert-butyl methyl(2-(methyl((3-(3-(3-methylbut-2-enamido)phenyl)-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazol-4-yl)methyl)amino)ethyl)carbamate

Product 1

HCID 904244883-methyl-N-(3-(4-((methyl(2-(methylamino)ethyl)amino)methyl)-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazol-3-yl)phenyl)but-2-enamideYield 33%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A solution of tert-butyl methyl(2-(methyl((3-(3-(3-methylbut-2-enamido)phenyl)-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazol-4-yl)methyl)amino)ethyl)carbamate (0.08 g, 0.000228 mol) in methanolic HCl (2 mL, 4M) was stirred for 1 hr at room temperature. The solution was concentrated under reduce pressure and triturated with diethyl ether to give 3-methyl-N-(3-(4-((methyl(2-(methylamino)ethyl)amino)methyl)-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazol-3-yl)phenyl)but-2-enamide (0.026 g, yield: 33%, HCl salt). 1H NMR (400 MHz, DMSO-d6): δ 8.02-7.80 (m, 2H), 7.60-7.50 (m, 1H), 7.44-7.35 (m, 1H), 7.30-7.21 (m, 1H), 5.90 (s, 1H), 4.50-4.20 (s, 2H), 3.30-3.00 (m), 2.60 (s, 3H), 2.52 (s, 3H), 2.15 (s, 3H), 1.88 (s, 3H) ppm. LCMS (ESI): RT=1.49 min, m/z=342.4 [M+H]+.

Workup

  1. concentrationThe solution was concentrated
  2. customtriturated with diethyl ether

Sources & evidence

ORD record
ord-a5c429d7fa9b4233a9c932614219e922
Source dataset
uspto-grants-2015_05
Patent number
US09023883B2

Reaction notes

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