Ethyl bromoacetate → [5-Chloro-3-(2-ethoxycarbonylmethyl-1,1-dioxo-2,3-dihydro-1h-1lambda6-benzo[d]isothiazol-3-yl)-2-methyl-indol-1-yl]-acetic acid

HRID 750671Notes

Reaction equation

C([O:5][C:6](=[O:30])[CH2:7][N:8]1[C:16]2[C:11](=[CH:12][C:13]([Cl:17])=[CH:14][CH:15]=2)[C:10]([CH:18]2[C:22]3[CH:23]=[CH:24][CH:25]=[CH:26][C:21]=3[S:20](=[O:28])(=[O:27])[NH:19]2)=[C:9]1[CH3:29])(C)(C)C.Br[CH2:32][C:33]([O:35][CH2:36][CH3:37])=[O:34]>>[Cl:17][C:13]1[CH:12]=[C:11]2[C:16](=[CH:15][CH:14]=1)[N:8]([CH2:7][C:6]([OH:30])=[O:5])[C:9]([CH3:29])=[C:10]2[CH:18]1[C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][C:21]=2[S:20](=[O:28])(=[O:27])[N:19]1[CH2:32][C:33]([O:35][CH2:36][CH3:37])=[O:34]

Participants

Reactant 2

HCID 7748Ethyl bromoacetate

HCID 67316509HCID 67316509, compound

Product 1

HCID 11569144[5-Chloro-3-(2-ethoxycarbonylmethyl-1,1-dioxo-2,3-dihydro-1h-1lambda6-benzo[d]isothiazol-3-yl)-2-methyl-indol-1-yl]-acetic acid

Procedure

The title compound was prepared by the method described for example 14 using the product from example 6, step c) and ethyl bromoacetate. 1H NMR (DMSO-d6) 13.15 (bs, 1H), 8.07-8.03 (m, 1H), 7.70-7.63 (m, 2H), 7.44 (d, J=8.7 Hz, 1H), 7.12 (d, J=8.1 Hz, 1H), 7.02 (dd, J=1.8, 8.7 Hz, 1H), 6.72 (s, 1H), 6.28 (s, 1H), 5.03 (s, 2H), 4.05-3.92 (m, 2H), 3.41 (q, J=6.9 Hz, 2H), 1.05 (t, J=6.9 Hz, 3H); MS: ESI (negative): 475, 477 (M−H).

Sources & evidence

ORD record: ord-a59c439755754fd3af4d87456c424e8e
Source dataset: uspto-grants-2008_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07405215B2

Reaction notes

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