N,N-Dimethylpropargylamine → HCID 57885917, compound

HRID 659422Notes

Reaction equation

HRID 659422 reaction equation
[Cl:1][C:2]1[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][C:3]=1[CH2:4][N:5]1[CH2:10][CH2:9][NH:8][C:7]2[N:11]=[CH:12][C:13](I)=[CH:14][C:6]1=2.[CH3:21][N:22]([CH3:26])[CH2:23][C:24]#[CH:25]>>[Cl:1][C:2]1[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][C:3]=1[CH2:4][N:5]1[CH2:10][CH2:9][NH:8][C:7]2[N:11]=[CH:12][C:13]([C:25]#[C:24][CH2:23][N:22]([CH3:26])[CH3:21])=[CH:14][C:6]1=2

Participants

3

Reactant 2

HCID 81643N,N-DimethylpropargylamineHCID 578860791-(2,5-Dichlorobenzyl)-7-iodo-3,4-dihydro-1H-pyrido[2,3-b]pyrazine

Product 1

HCID 57885917HCID 57885917, compoundYield 49%

Procedure

1-(2,5-Dichlorobenzyl)-7-iodo-1,2,3,4-tetrahydropyrido[2,3-b]pyrazine (113 mg) was coupled with 1-dimethylamino-2-propyne as in General Procedure 5 to give the title compound as a yellow solid (49% yield). M.p.=168° C., LCMS: m/z=375.08 (M+H+), 1H-NMR (CDCl3, 400 MHz) δ 2.31 (6H, s), 3.38 (4H, m), 3.61 (2H, t, J=4.0 Hz), 4.40 (2H, s), 5.54 (1H, bs), 6.45 (1H, d, J=1.5 Hz), 7.21 (2H, m), 7.33 (1H, m), 7.61 (1H, d, J=1.5 Hz).

Sources & evidence

ORD record
ord-e8a2652c5c2045fa800768a179354aa8
Source dataset
uspto-grants-2011_12
Patent number
US08080561B2

Reaction notes

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