Diisopropylethylamine → HCID 67041569, compound

HRID 62758Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([O:12][CH:13]([CH3:15])[CH3:14])[C:10]=1[Cl:11])[C:5]([OH:7])=O.CCN(C(C)C)C(C)C.[NH2:25][C:26]1[CH:35]=[CH:34][C:29]([C:30]([O:32][CH3:33])=[O:31])=[C:28]([CH3:36])[CH:27]=1>>[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([O:12][CH:13]([CH3:15])[CH3:14])[C:10]=1[Cl:11])[C:5]([NH:25][C:26]1[CH:35]=[CH:34][C:29]([C:30]([O:32][CH3:33])=[O:31])=[C:28]([CH3:36])[CH:27]=1)=[O:7]

Participants

Reactant 3

HCID 81531Diisopropylethylamine

HCID 11672721Methyl 4-amino-2-methylbenzoate

HCID 67041592HCID 67041592, compound

Product 1

HCID 67041569HCID 67041569, compoundYield 68%

Procedure

Methyl 4-(3,4-dichloro-5-isopropoxybenzamido)-2-methylbenzoate (10) (237 mg, 68%) was prepared from 3,4-dichloro-5-isopropoxybenzoic acid (8) (200 mg, 800 μmol) using a procedure essentially the same as in step (i) for AAA-064 except that DIPEA was used instead of TEA, and methyl 4-amino-2-methylbenzoate (9) was used instead of methyl 4-amino-2-fluorobenzoate: m/z 396 [M+H]+ (ES+), 394 [M−H]− (ES−), 1H NMR (400 MHz, DMSO-d6) δ: 10.51 (1H, s), 7.89 (1H, d), 7.81 (1H, d), 7.77-7.72 (2H, m), 7.64 (1H, d), 4.85 (1H, sep), 3.81 (3H, s), 2.54 (3H, s), 1.35 (6H, d).

Sources & evidence

ORD record: ord-01ad598122fe493395911dc990ecb5e0
Source dataset: uspto-grants-2016_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09447028B2

Reaction notes

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