Benzenemethanamine, 3,4-dichloro- → HCID 54678888, compound

HRID 458702Notes

Reaction equation

HRID 458702 reaction equation
[CH3:1][N:2]1[C:7]2=[N:8][C:9]([C:14]([O:16]CC)=O)=[C:10]([OH:13])[C:11](=[O:12])[N:6]2[CH2:5][C:4](=[O:19])[N:3]1[CH3:20].[Cl:21][C:22]1[CH:23]=[C:24]([CH:27]=[CH:28][C:29]=1[Cl:30])[CH2:25][NH2:26]>>[Cl:21][C:22]1[CH:23]=[C:24]([CH:27]=[CH:28][C:29]=1[Cl:30])[CH2:25][NH:26][C:14]([C:9]1[N:8]=[C:7]2[N:6]([C:11](=[O:12])[C:10]=1[OH:13])[CH2:5][C:4](=[O:19])[N:3]([CH3:20])[N:2]2[CH3:1])=[O:16]

Participants

3

Reactant 2

HCID 1608Benzenemethanamine, 3,4-dichloro-HCID 54725630HCID 54725630, compound

Product 1

HCID 54678888HCID 54678888, compoundYield 74%

Procedure

Reaction of intermediate 22, ethyl 1,2-dimethyl-7-hydroxy-3,6-dioxo-2,3,4,6-tetrahydro-1H-pyrimido[2,1-c][1,2,4]triazine-8-carboxylate, (0.050 g, 0.177 mmol) with 3,4-dichlorobenzylamine (0.10 g, 0.57 mmol) as described in the preparation of example 1 gave 0.054 g (74% yield) of the title amide as a white solid. 1HNMR 400 MHz (CDCl3) δ (ppm): 3.28 (3H, s, NCH3), 3.32 (3H, s, NCH3), 4.59 (2H, d, J=6.7 Hz, NCH2), 4.68 (2H, s, CH2), 7.21 (1H, dd, J=2.0 Hz and J=8.0 Hz, aromatic), 7.44 (1H, d, J=2.0 Hz, aromatic), 7.46 (1H, d, J=8.0 Hz, aromatic), 7.78 (1H, broad t, NH), 11.85 (1H, s, OH). MS (ESI+) m/z 413 [M+H+].

Workup

  1. customas described in the preparation of example 1

Sources & evidence

ORD record
ord-607062415ff04845a7de86801fdb3a5f
Source dataset
uspto-grants-2007_03
Patent number
US07192948B2

Reaction notes

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