2-(4-bromobutyl)-1H-benzo[de]isoquinoline-1,3(2H)-dione → HCID 73296092, compound

HRID 2172661Notes

Reaction equation

HRID 2172661 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][CH2:20][N:21]1[C:30](=[O:31])[C:29]2[CH:32]=[CH:33][CH:34]=[C:27]3[C:28]=2[C:23](=[CH:24][CH:25]=[CH:26]3)[C:22]1=[O:35]>>[O:35]=[C:22]1[C:23]2[C:28]3[C:27](=[CH:34][CH:33]=[CH:32][C:29]=3[C:30](=[O:31])[N:21]1[CH2:20][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:26]=[CH:25][CH:24]=2

Participants

3

Reactant 2

HCID 27823602-(4-bromobutyl)-1H-benzo[de]isoquinoline-1,3(2H)-dioneHCID 4652880Ethyl 2-(Aminosulfonyl)benzoate

Product 1

HCID 73296092HCID 73296092, compound

Procedure

The compound was prepared according to GP-2 using 2-sulfamoylbenzoic acid ethyl ester 4 and compound 3b. The crude product was purified by flash column chromatography using MeOH—CHCl3 to obtain 5b. 1H NMR (500 MHz, DMSO-d6) δ 9.27 (bs, 2H), 8.49-8.45 (m, 4H), 7.87 (t, J=8.0 Hz, 2H), 7.69 (d, J=8.0 Hz 1H), 7.63 (d, J=8.0 Hz 1H), 7.44 (t, J=7.5 Hz, 1H), 7.32 (t, J=7.5 Hz, 1H), 3.99 (t, J=7.0, 2H), 2.71 (q, J=7.0 Hz, 2H), 1.64-1.56 (m, 2H), 1.46-1.38 (m, 2H). MS (ES−) m/z 451 (M−H)−.

Workup

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

Sources & evidence

ORD record
ord-221055319edf44aa85ca79c977496f65
Source dataset
uspto-grants-2015_06
Patent number
US09056835B2

Reaction notes

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