Hydrochloric Acid → HCID 10453291, compound

HRID 2373482Notes

Reaction equation

C([O:4][CH2:5][C:6]1[N:7]([CH2:27][C:28]2[CH:33]=[CH:32][C:31]([CH3:34])=[CH:30][CH:29]=2)[C:8]2[C:13]([C:14]=1[C:15](=[O:19])[C:16](O)=[O:17])=[CH:12][C:11]([C:20]1[CH:25]=[CH:24][CH:23]=[C:22]([CH3:26])[CH:21]=1)=[CH:10][CH:9]=2)(=O)C.[OH-].[K+].Cl>>[CH3:34][C:31]1[CH:32]=[CH:33][C:28]([CH2:27][N:7]2[C:8]3[C:13](=[CH:12][C:11]([C:20]4[CH:25]=[CH:24][CH:23]=[C:22]([CH3:26])[CH:21]=4)=[CH:10][CH:9]=3)[C:14]3[C:15](=[O:19])[C:16](=[O:17])[O:4][CH2:5][C:6]2=3)=[CH:29][CH:30]=1

Participants

Reactant 3

HCID 313Hydrochloric Acid

HCID 14797Potassium Hydroxide

HCID 21964301HCID 21964301, compound

Product 1

HCID 10453291HCID 10453291, compound

Procedure

The title compound was prepared from [2-[(acetyloxy)methyl]-1-(4-methylbenzyl)-5-(3-methylphenyl)-1H-indol-3-yl](oxo)acetic acid and aqueous potassium hydroxide in substantially the same manner, as described in step 6 of Example 1 followed by the treatment with aqueous HCl in substantially the same manner, as described in step 7 of Example 1. The product was obtained as a white solid; mp: 216-217° C. Mass spectrum (ESI, [M+H]+) m/z 396. 1H NMR (400 MHz, DMSO-d6) δ 8.21 (s, 1H), 7.71 (d, 1H, J=8.56 Hz), 7.64 (dd, 1H, J=8.75 and 1.28 Hz), 7.49 (s, 1H), 7.46 (d, 1H, J=8.09 Hz), 7.36 (t, 1H, J=7.63 Hz), 7.19-7.14 (m, 5H,), 5.91 (s, 2H), and 5.49 (s, 2H), 2.39 (s, 3H), 2.26 ppm (s, 3H),

Workup

customThe product was obtained as a white solid

Sources & evidence

ORD record: ord-35e7a70f6b434724be7f0a82d237c030
Source dataset: uspto-grants-2008_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07459478B2

Reaction notes

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