Dimethylsulphamoyl chloride → HCID 58213767, compound

HRID 340373Notes

Reaction equation

[NH2:1][C:2]1[C:11]2[N:10]=[CH:9][C:8]([CH2:12][CH2:13][C:14]3[CH:19]=[CH:18][C:17]([OH:20])=[CH:16][C:15]=3[CH3:21])=[CH:7][C:6]=2[C:5]2[CH:22]=[CH:23][C:24]([CH3:26])=[CH:25][C:4]=2[N:3]=1.[CH3:27][N:28]([CH3:33])[S:29](Cl)(=[O:31])=[O:30]>>[CH3:27][N:28]([CH3:33])[S:29](=[O:31])(=[O:30])[O:20][C:17]1[CH:18]=[CH:19][C:14]([CH2:13][CH2:12][C:8]2[CH:9]=[N:10][C:11]3[C:2]([NH2:1])=[N:3][C:4]4[CH:25]=[C:24]([CH3:26])[CH:23]=[CH:22][C:5]=4[C:6]=3[CH:7]=2)=[C:15]([CH3:21])[CH:16]=1

Participants

Reactant 2

HCID 83372Dimethylsulphamoyl chloride

HCID 581665094-(2-(5-Amino-8-methylbenzo[f][1,7]naphthyridin-2-yl)ethyl)-3-methylphenol

Product 1

HCID 58213767HCID 58213767, compound

Procedure

4-(2-(5-Amino-8-methylbenzo[f][1,7]naphthyridin-2-yl)ethyl)-3-methylphenyl dimethylsulfamate was prepared from 4-(2-(5-amino-8-methylbenzo[f][1,7]naphthyridin-2-yl)ethyl)-3-methylphenol (from Example 50) following the procedure described for Example 138, but using dimethylsulfamoyl chloride. 1H NMR (Acetone-d6): δ 8.79 (s, 1H), 8.72 (s, 1H), 8.28 (d, 1H), 7.42 (s, 1H), 7.27 (d, 1H), 7.17 (s, 1H), 7.14 (t, 1H), 7.05-7.10 (d, 1H), 3.19-3.25 (m, 2H), 3.11-3.17 (m, 2H), 2.92 (s, 6H), 2.46 (s, 3H), 2.37 (s, 3H). LRMS [M+H]=451.2.

Sources & evidence

ORD record: ord-5a21a4449a744ec99889cb1b0b9ca1a6
Source dataset: uspto-grants-2014_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08895577B2

Reaction notes

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