2-Methoxyethylamine → HCID 11271449, compound

HRID 403053Notes

Reaction equation

HRID 403053 reaction equation
[CH:1]1([NH:4][C:5](=[O:31])[C:6]2[CH:11]=[CH:10][C:9]([CH3:12])=[C:8]([NH:13][C:14](=[O:30])[C:15]3[CH:20]=[CH:19][C:18]([O:21][CH2:22][C:23]4[CH:28]=[CH:27][CH:26]=[C:25](Br)[N:24]=4)=[CH:17][CH:16]=3)[CH:7]=2)[CH2:3][CH2:2]1.[CH3:32][O:33][CH2:34][CH2:35][NH2:36]>CN1C(=O)CCC1>[CH:1]1([NH:4][C:5](=[O:31])[C:6]2[CH:11]=[CH:10][C:9]([CH3:12])=[C:8]([NH:13][C:14](=[O:30])[C:15]3[CH:20]=[CH:19][C:18]([O:21][CH2:22][C:23]4[CH:28]=[CH:27][CH:26]=[C:25]([NH:36][CH2:35][CH2:34][O:33][CH3:32])[N:24]=4)=[CH:17][CH:16]=3)[CH:7]=2)[CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 80182-MethoxyethylamineHCID 11409007HCID 11409007, compound

Product 1

HCID 11271449HCID 11271449, compound

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
190 °C

Procedure

A mixture of N-cyclopropyl-4-methyl-3-({4-[(6-bromo-2-pyridinyl)methoxy]benzoyl}amino)benzamide (100 mg, 0.21 mmol), 2-methoxyethylamine (500 μL) and NMP (500 μL) was heated to 190° C. in the microwave for 90 min. The cooled reaction mixture was eluted through a silica cartridge with isohexane then ethyl acetate to give the crude product which was triturated with diethyl ether to give the title compound as a solid (36 mg); NMR Spectrum: (DMSOd6) 0.57 (m, 2H), 0.68 (m, 2H), 2.27 (s, 3H), 2.85 (m, 1H), 3.28 (m, 2H), 3.31 (m, 3H), 5.08 (s, 2H), 6.47 (d, 1H), 6.61 (d, 2H), 7.14 (d, 2H), 7.32 (m, 2H), 7.40 (m, 1H), 7.63 (m, 1H), 7.80 (m, 2H), 7.97 (m, 2H), 8.37 (m, 1H), 9.84 (s, 1H); Mass Spectrum: M+H+ 475.

Workup

  1. customThe cooled reaction mixture
  2. washwas eluted through a silica cartridge with isohexane
  3. customethyl acetate to give the crude product which
  4. customwas triturated with diethyl ether

Sources & evidence

ORD record
ord-6ba8841c6b1b4b61aa78973818375ff0
Source dataset
uspto-grants-2014_06
Patent number
US08742124B2

Reaction notes

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