2-Bromopropane → 4-(3-Chloro-4,5-diisopropoxybenzamido)-2-methylbenzoic acid

HRID 62739Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[C:4]([CH:17]=[C:18]([O:24][CH:25]([CH3:27])[CH3:26])[C:19]=1[O:20][CH:21]([CH3:23])[CH3:22])[C:5]([NH:7][C:8]1[CH:16]=[CH:15][C:11]([C:12]([OH:14])=[O:13])=[CH:10][CH:9]=1)=[O:6].[CH:28](Br)(C)C.NC1C=CC(C(OC)=O)=C(C)C=1>>[Cl:1][C:2]1[CH:3]=[C:4]([CH:17]=[C:18]([O:24][CH:25]([CH3:27])[CH3:26])[C:19]=1[O:20][CH:21]([CH3:22])[CH3:23])[C:5]([NH:7][C:8]1[CH:9]=[CH:10][C:11]([C:12]([OH:14])=[O:13])=[C:15]([CH3:28])[CH:16]=1)=[O:6]

Participants

Reactant 3

HCID 63582-Bromopropane

HCID 11672721Methyl 4-amino-2-methylbenzoate

HCID 510339724-(3-Chloro-4,5-diisopropoxybenzamido)benzoic acid

Product 1

HCID 510339734-(3-Chloro-4,5-diisopropoxybenzamido)-2-methylbenzoic acid

Procedure

4-(3-Chloro-4,5-diisopropoxybenzamido)benzoic acid (AAA-051) (103 mg, 48% for final step) was prepared in essentially the same manner as AAA-044 except isopropyl bromide was used instead of cyclopentyl iodide and the reaction performed at 80° C. in step (iii) and that methyl 4-amino-2-methylbenzoate was used instead of methyl 4-aminobenzoate in step (v): m/z 404 [M−H]− (ES−); 1H NMR (400 MHz, DMSO-d6) δ: 12.62 (1H, br s), 10.34 (1H, s), 7.87 (1H, d), 7.73 (1H, dd), 7.68 (2H, d), 7.54 (1H, d), 4.76 (1H, m), 4.59 (1H, m), 2.54 (3H, s), 1.33 (6H, d), 1.28 (6H, d).

Workup

customperformed at 80° C. in step (iii)

Sources & evidence

ORD record: ord-1301fb9f6640441d97c0ff1b990593fa
Source dataset: uspto-grants-2016_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09447028B2

Reaction notes

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