2-Chlorobenzenesulfonyl chloride → HCID 57885982, compound

HRID 659394Notes

Reaction equation

HRID 659394 reaction equation
[I:1][C:2]1[CH:11]=[N:10][C:5]2[NH:6][CH2:7][CH2:8][NH:9][C:4]=2[CH:3]=1.[Cl:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[S:19](Cl)(=[O:21])=[O:20]>N1C=CC=CC=1>[Cl:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[S:19]([N:9]1[CH2:8][CH2:7][NH:6][C:5]2[N:10]=[CH:11][C:2]([I:1])=[CH:3][C:4]1=2)(=[O:21])=[O:20]

Participants

4

Reactant 2

HCID 761872-Chlorobenzenesulfonyl chlorideHCID 578861297-Iodo-1,2,3,4-tetrahydropyrido[2,3-b]pyrazine

Product 1

HCID 57885982HCID 57885982, compoundYield 10%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
100 °C

Procedure

7-Iodo-1,2,3,4-tetrahydropyrido[2,3-b]pyrazine (300 mg) was dissolved in anhydrous pyridine. 2-chlorobenzene sulfonyl chloride (1.0 eq) was added and the reaction mixture was heated to 100° C. in a microwave oven for 10 minutes. Silica gel chromatography gave the title compound as a pale orange solid (10% yield). M.p. 146-147° C., LCMS: m/z=435.94 (M+H+), 1H-NMR (CDCl3, 400 MHz) δ 3.30-3.35 (m, 2H), 3.80 (t, J=5.0 Hz, 2H), 5.02 (bs, 1H), 7.42-4.57 (m, 3H), 7.81 (d, J=1.8 Hz, 1H), 8.00 (d, J=1.8 Hz, 1H), 8.10 (dd, J=8.6 Hz, 1.5 Hz, 1H).

Sources & evidence

ORD record
ord-8697110ba58c4465a0bcf229d2fef6bc
Source dataset
uspto-grants-2011_12
Patent number
US08080561B2

Reaction notes

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