tert-butyl (2-(((3-(4-methacrylamidophenyl)-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazol-4-yl)methyl)(methyl)amino)ethyl)(methyl)carbamate → HCID 178454443, compound

HRID 570783Notes

Reaction equation

HRID 570783 reaction equation
[C:1]([NH:6][C:7]1[CH:12]=[CH:11][C:10]([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:9][CH:8]=1)(=[O:5])[C:2]([CH3:4])=[CH2:3]>Cl>[CH3:31][N:19]([CH2:18][C:17]1[C:13]([C:10]2[CH:9]=[CH:8][C:7]([NH:6][C:1](=[O:5])[C:2]([CH3:4])=[CH2:3])=[CH:12][CH:11]=2)=[N:14][NH:15][CH:16]=1)[CH2:20][CH2:21][NH:22][CH3:23]

Participants

3

Reactant 1

HCID 117617843tert-butyl (2-(((3-(4-methacrylamidophenyl)-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazol-4-yl)methyl)(methyl)amino)ethyl)(methyl)carbamate

Product 1

HCID 178454443HCID 178454443, compoundYield 81.4%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A solution of tert-butyl (2-(((3-(4-methacrylamidophenyl)-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazol-4-yl)methyl)(methyl)amino)ethyl)(methyl)carbamate (0.08 g, 0.00015 mol) in methanolic HCl (2 mL, 4M solution) was stirred for 1 hr at room temperature. The reaction mixture was concentrated under vacuum and purified by prep HPLC using water:ACN as mobile phase (containing 0.1% TFA as modifier) to obtain N-(4-(4-((methyl(2-(methylamino)ethyl)amino)methyl)-1H-pyrazol-3-yl)phenyl)methacrylamide (0.040 g, yield: 80%). 1H NMR (400 MHz, CD3OD): δ 7.98 (s, 1H), 7.84-7.81 (m, 2H), 7.59-7.56 (d, 2H), 5.85 (s, 1H) 5.58 (s, 1H), 5.52 (s, 1H), 4.51 (s, 2H), 3.37 (s), 2.72 (s, 3H), 2.70 (s, 3H), 2.06 (s, 3H) ppm; LCMS (ESI): RT=1.63 min, m/z=328.3 [M+H]+.

Workup

  1. concentrationThe reaction mixture was concentrated under vacuum
  2. custompurified by prep HPLC
  3. additionACN as mobile phase (containing 0.1% TFA as modifier)

Sources & evidence

ORD record
ord-bebc6cd885e54c8b9c175180f582dce3
Source dataset
uspto-grants-2015_05
Patent number
US09023883B2

Reaction notes

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