4-(Prop-2-yn-1-yl)-1lambda~6~,4-thiazinane-1,1-dione → HCID 57886090, compound

HRID 659423Notes

Reaction equation

HRID 659423 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.[CH2:21]([N:24]1[CH2:29][CH2:28][S:27](=[O:31])(=[O:30])[CH2:26][CH2:25]1)[C:22]#[CH:23]>>[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:23]#[C:22][CH2:21][N:24]3[CH2:25][CH2:26][S:27](=[O:31])(=[O:30])[CH2:28][CH2:29]3)=[CH:14][C:6]1=2

Participants

3

Reactant 2

HCID 27772654-(Prop-2-yn-1-yl)-1lambda~6~,4-thiazinane-1,1-dioneHCID 578860791-(2,5-Dichlorobenzyl)-7-iodo-3,4-dihydro-1H-pyrido[2,3-b]pyrazine

Product 1

HCID 57886090HCID 57886090, compoundYield 34%

Procedure

1-(2,5-Dichlorobenzyl)-7-iodo-1,2,3,4-tetrahydropyrido[2,3-b]pyrazine (108 mg) was coupled with 4-prop-2-ynyl-thiomorpholine 1,1-dioxide as in General Procedure 5 to give the title compound as an off-white solid (34% yield). M.p.>200° C., LCMS: m/z=467.33 (M+H+), 1H-NMR (CDCl3, 400 MHz) δ 3.11 (8H, s), 3.40 (2H, t, J=4.8 Hz), 3.56 (2H, s), 3.61 (2H, t, J=4.7 Hz), 4.41 (2H, s), 6.42 (1H, dt, J=1.5 Hz), 7.22 (2H, m), 7.35 (1H, d, J=8.3 Hz), 7.58 (1H, d, J=1.5 Hz).

Sources & evidence

ORD record
ord-20f7bc382d4f4072a12031d420de98c7
Source dataset
uspto-grants-2011_12
Patent number
US08080561B2

Reaction notes

Loading…