Methyl 4-(3-chloro-5-isopropoxy-4-methoxybenzamido)-2-methylbenzoate → HCID 51034299, compound

HRID 62748Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[C:4]([CH:19]=[C:20]([O:24][CH:25]([CH3:27])[CH3:26])[C:21]=1[O:22][CH3:23])[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:24][CH:25]([CH3:27])[CH3:26])[C:21]=1[O:22][CH3:23])[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-Chloro-5-isopropoxy-4-methoxybenzamido)-2-methylbenzoic acid (AAA-075) (94 mg, 57%) was prepared from methyl 4-(3-chloro-5-isopropoxy-4-methoxybenzamido)-2-methylbenzoate (7) (167 mg, 4.10 mmol) using a procedure essentially the same as in step (ii) for AAA-001 except that MeOH was added dropwise until a solution formed and the mixture was stirred at 40° C. for 18 h: m/z 378 [M+H]+ (ES+), 376 [M−H]− (ES−). 1H NMR (400 MHz, DMSO-d6) δ:12.63 (1H, br s), 10.34 (1H, s), 7.86 (1H, d), 7.75-7.63 (3H, m), 7.57 (1H, d), 4.77 (1H, sep), 3.83 (3H, s), 2.53 (3H, s), 1.34 (6H, d).

Workup

additionwas added dropwise until a solution
customformed

Sources & evidence

ORD record: ord-85ef2ebad5544e42aa641826696df3a5
Source dataset: uspto-grants-2016_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09447028B2

Reaction notes

Loading…