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

HRID 570782Notes

Reaction equation

HRID 570782 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:12]([CH2:13][N:14]([CH3:26])[CH2:15][CH2:16][N:17]([CH3:25])[C:18](=[O:24])[O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[CH:11][N:10]([CH:27]3[CH2:32][CH2:31][CH2:30][CH2:29][O:28]3)[N:9]=2)=[CH:4][CH:3]=1.[C:33](Cl)(=[O:37])[C:34]([CH3:36])=[CH2:35].O>C(Cl)Cl.CO>[C:33]([NH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:12]([CH2:13][N:14]([CH3:26])[CH2:15][CH2:16][N:17]([CH3:25])[C:18](=[O:24])[O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[CH:11][N:10]([CH:27]3[CH2:32][CH2:31][CH2:30][CH2:29][O:28]3)[N:9]=2)=[CH:4][CH:3]=1)(=[O:37])[C:34]([CH3:36])=[CH2:35]

Participants

6

Reactant 3

HCID 962WaterHCID 13528Methacryloyl chlorideHCID 90434027tert-butyl (2-(((3-(4-aminophenyl)-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazol-4-yl)methyl)(methyl)amino)ethyl)(methyl)carbamate

Product 1

HCID 117617843tert-butyl (2-(((3-(4-methacrylamidophenyl)-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazol-4-yl)methyl)(methyl)amino)ethyl)(methyl)carbamateYield 46.3%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

A solution of tert-butyl (2-(((3-(4-aminophenyl)-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazol-4-yl)methyl)(methyl)amino)ethyl)(methyl)carbamate (0.150 g, 0.000338 mol) in DCM (3 mL) was cooled to 0° C. TEA (0.068 g, 0.000677 mol) and methacryloyl chloride (0.042 g, 0.000406 mol) were added and the reaction mixture stirred for 15 mins at 0° C. The reaction was poured into water (25 mL) and extracted with EtOAc (20 mL×2). The combined extracts was washed with brine (30 mL), dried over sodium sulphate and concentrated under vacuum. The residue was purified by SGC using DCM:MeOH (0%-5%) as eluent to obtain tert-butyl (2-(((3-(4-methacrylamidophenyl)-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazol-4-yl)methyl)(methyl)amino)ethyl)(methyl)carbamate (0.080 g, Yield: 45%). ESI-MS: m/z=512.3 [M+1]+.

Workup

  1. extractionextracted with EtOAc (20 mL×2)
  2. washThe combined extracts was washed with brine (30 mL)
  3. dry with materialdried over sodium sulphate
  4. concentrationconcentrated under vacuum
  5. customThe residue was purified by SGC

Sources & evidence

ORD record
ord-3a3d574015c448f98215480b9a79eb04
Source dataset
uspto-grants-2015_05
Patent number
US09023883B2

Reaction notes

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