Ethyl 2-(Aminosulfonyl)benzoate → HCID 73053706, compound

HRID 2172660Notes

Reaction equation

HRID 2172660 reaction equation
C([O:3][C:4](=[O:15])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[S:11](=[O:14])(=[O:13])[NH2:12])C.Br[CH2:17][CH2:18][CH2:19][N:20]1[C:29](=[O:30])[C:28]2[CH:31]=[CH:32][CH:33]=[C:26]3[C:27]=2[C:22](=[CH:23][CH:24]=[CH:25]3)[C:21]1=[O:34]>>[O:34]=[C:21]1[C:22]2[C:27]3[C:26](=[CH:33][CH:32]=[CH:31][C:28]=3[C:29](=[O:30])[N:20]1[CH2:19][CH2:18][CH2:17][NH:12][S:11]([C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=1[C:4]([OH:3])=[O:15])(=[O:13])=[O:14])[CH:25]=[CH:24][CH:23]=2

Participants

3

Reactant 2

HCID 4652880Ethyl 2-(Aminosulfonyl)benzoateHCID 19029914HCID 19029914, compound

Product 1

HCID 73053706HCID 73053706, compound

Procedure

The compound was prepared according to GP-2 using 2-sulfamoylbenzoic acid ethyl ester 4 and compound 3a. The crude product was purified by flash column chromatography using MeOH—CHCl3 to obtain 5a. 1H NMR (500 MHz, DMSO-d6) δ 9.43 (bs, 2H), 8.49-8.46 (m, 4H), 7.87 (t, J=8.0 Hz, 2H), 7.68 (d, J=7.5 Hz 1H), 7.64 (d, J=8.0 Hz 1H), 7.49 (t, J=7.5 Hz, 1H), 7.33 (t, J=7.5 Hz, 1H), 4.02 (t, J=7.5, 2H), 2.76 (q, J=7.0 Hz, 2H), 1.90-1.60 (m, 2H). MS (ES−) m/z 437 (M−H)−.

Workup

  1. customThe compound was prepared
  2. customThe crude product was purified by flash column chromatography

Sources & evidence

ORD record
ord-ebcf33e6cef345fcb56a7f2d45cbce71
Source dataset
uspto-grants-2015_06
Patent number
US09056835B2

Reaction notes

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