Methyl 4-(4-chloro-3-isopropoxy-5-methoxybenzamido)benzoate → HCID 67041948, compound

HRID 62770Notes

Reaction equation

HRID 62770 reaction equation
[Cl:1][C:2]1[C:20]([O:21][CH3:22])=[CH:19][C:5]([C:6]([NH:8][C:9]2[CH:18]=[CH:17][C:12]([C:13]([O:15]C)=[O:14])=[CH:11][CH:10]=2)=[O:7])=[CH:4][C:3]=1[O:23][CH:24]([CH3:26])[CH3:25]>O1CCOCC1>[Cl:1][C:2]1[C:20]([O:21][CH3:22])=[CH:19][C:5]([C:6]([NH:8][C:9]2[CH:10]=[CH:11][C:12]([C:13]([OH:15])=[O:14])=[CH:17][CH:18]=2)=[O:7])=[CH:4][C:3]=1[O:23][CH:24]([CH3:26])[CH3:25]

Participants

3

Reactant 1

HCID 67041570Methyl 4-(4-chloro-3-isopropoxy-5-methoxybenzamido)benzoate

Product 1

HCID 67041948HCID 67041948, compoundYield 57.3%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

4-(4-Chloro-3-isopropoxy-5-methoxybenzamido)benzoic acid (AAA-118) (10 mg, 55%) was prepared from methyl 4-(4-chloro-3-isopropoxy-5-methoxybenzamido)benzoate (5) (20 mg, 48 μmol) using a procedure essentially the same as in step (ii) for AAA-001 except that dioxane (3 mL) was used instead of THF: m/z 362 [M−H]− (ES−); 1H NMR (400 MHz, DMSO-d6) δ: 12.80 (1H, br s), 10.47 (1H, s), 7.99-7.92 (2H, m), 7.90-7.83 (2H, m), 7.31 (2H, dd), 4.79 (1H, sep), 3.94 (3H, s), 1.33 (6H, d).

Sources & evidence

ORD record
ord-fd7bb18b59984164a13c837fa8b3433f
Source dataset
uspto-grants-2016_09
Patent number
US09447028B2

Reaction notes

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