HCID 67041569, compound → 4-(3,4-Dichloro-5-isopropoxybenzamido)-2-methylbenzoic acid

HRID 62759Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[C:4]([CH:19]=[C:20]([O:23][CH:24]([CH3:26])[CH3:25])[C:21]=1[Cl:22])[C:5]([NH:7][C:8]1[CH:17]=[CH:16][C:11]([C:12]([O:14]C)=[O:13])=[C:10]([CH3:18])[CH:9]=1)=[O:6]>CO>[Cl:1][C:2]1[CH:3]=[C:4]([CH:19]=[C:20]([O:23][CH:24]([CH3:26])[CH3:25])[C:21]=1[Cl:22])[C:5]([NH:7][C:8]1[CH:17]=[CH:16][C:11]([C:12]([OH:14])=[O:13])=[C:10]([CH3:18])[CH:9]=1)=[O:6]

Participants

Conditions

Temperature: 40 °C

Procedure

4-(3,4-Dichloro-5-isopropoxybenzamido)-2-methylbenzoic acid (AAA-113) (85 mg, 41%) was prepared from methyl 4-(3,4-dichloro-5-isopropoxybenzamido)-2-methylbenzoate (10) (210 mg, 0.530 mmol) using a procedure essentially the same as in step (ii) for AAA-001 except that MeOH was added dropwise to obtain a solution and the mixture was stirred at 40° C. for 20 h: m/z 380 [M−H]− (ES−), 1H NMR (400 MHz, DMSO-d6) δ: 12.66 (1H, br s), 10.48 (1H, s), 7.88 (1H, d), 7.81 (1H, d), 7.75-7.66 (2H, m), 7.64 (1H, d), 4.86 (1H, sep), 2.54 (3H, s), 1.35 (6H, d).

Workup

additionwas added dropwise
customto obtain a solution

Sources & evidence

ORD record: ord-91c18c0a2e99488b8cda7c5b60cea7a3
Source dataset: uspto-grants-2016_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09447028B2

Reaction notes

Loading…