2-Methoxyethylamine → HCID 22291082, compound

HRID 1369509Notes

Reaction equation

[CH3:1][O:2][CH2:3][CH2:4][NH2:5].[C:6]([C:8]1[CH:34]=[CH:33][C:11]([C:12]([NH:14][C:15]2[CH:16]=[CH:17][C:18]([CH3:32])=[C:19]([NH:21][C:22](=[O:31])[C:23]3[CH:28]=[CH:27][C:26]([CH2:29]Cl)=[CH:25][CH:24]=3)[CH:20]=2)=[O:13])=[CH:10][CH:9]=1)#[N:7].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[C:6]([C:8]1[CH:9]=[CH:10][C:11]([C:12]([NH:14][C:15]2[CH:16]=[CH:17][C:18]([CH3:32])=[C:19]([NH:21][C:22](=[O:31])[C:23]3[CH:28]=[CH:27][C:26]([CH2:29][NH:5][CH2:4][CH2:3][O:2][CH3:1])=[CH:25][CH:24]=3)[CH:20]=2)=[O:13])=[CH:33][CH:34]=1)#[N:7]

Participants

Conditions

Temperature: 55 °C

Procedure

2-Methoxyethylamine (0.019 ml) was added to a stirred solution of N-[5-(4-cyanobenzamido)-2-methylphenyl]-4-(chloromethyl)benzamide (0.060 g) and potassium carbonate (0.041 g) in acetone (5 ml) and the reaction mixture was heated to 55° C. overnight. Further portions of 2-methoxyethylamine and potassium carbonate (same quantities as before) were added and the reaction mixture was stirred at 55° C. for a further 4 days. The reaction mixture was evaporated and the residue was triturated with water. The resultant solid was isolated and dried under vacuum at 55° C. to give the title compound as a solid (0.039 g, 59%); NMR Spectrum: (CDCl3) 2.27 (s, 3H), 2.83 (m, 2H), 3.37 (m, 4H), 3.56 (t, 2H), 3.91 (s, 2H), 7.19 (d, 1H), 7.49 (d, 2H), 7.77 (m, 7H), 7.95 (d, 2H), 8.13 (s, 1H), 8.3 (s, 1H); Mass Spectrum: M−H− 441.

Workup

customThe reaction mixture was evaporated
customthe residue was triturated with water
customThe resultant solid was isolated
customdried under vacuum at 55° C.

Sources & evidence

ORD record: ord-5b5ca42e53da4c60aba5c5d0d1fde2dc
Source dataset: uspto-grants-2003_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06579872B1

Reaction notes

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