4-Isopropylphenylboronic acid → HCID 68974707, compound

HRID 1272695Notes

Reaction equation

[CH3:1][O:2][C:3]([C:5]1[N:6]=[C:7]([CH2:16][CH:17]2[CH2:21][CH2:20][CH2:19][CH2:18]2)[C:8]2[C:13]([CH:14]=1)=[CH:12][CH:11]=[C:10]([OH:15])[CH:9]=2)=[O:4].[CH:22]([C:25]1[CH:30]=[CH:29][C:28](B(O)O)=[CH:27][CH:26]=1)([CH3:24])[CH3:23]>>[CH3:1][O:2][C:3]([C:5]1[N:6]=[C:7]([CH2:16][CH:17]2[CH2:21][CH2:20][CH2:19][CH2:18]2)[C:8]2[C:13]([CH:14]=1)=[CH:12][CH:11]=[C:10]([O:15][C:28]1[CH:29]=[CH:30][C:25]([CH:22]([CH3:24])[CH3:23])=[CH:26][CH:27]=1)[CH:9]=2)=[O:4]

Participants

Reactant 2

HCID 27734804-Isopropylphenylboronic acid

HCID 68869033HCID 68869033, compound

Product 1

HCID 68974707HCID 68974707, compound

Procedure

1-cyclopentylmethyl-7-hydroxy-isoquinoline-3-carboxylic acid methyl ester (prepared in example E-1) was treated with 4-isopropylphenylboronic acid by the general procedure G to yield 7-(4-isopropyl-phenoxy)-1-cyclopentylmethyl-isoquinoline-3-carboxylic acid methyl ester. This ester was hydrolyzed by the general procedure C to afford 7-(4-isopropyl-phenoxy)-1-cyclopentylmethyl-isoquinoline-3-carboxylic acid. This acid was coupled with Compound E-6 by the general procedure A to yield 2(S)-{[1-cyclopentylmethyl-7-(4-isopropyl-phenoxy)-isoquinoline-3-carbonyl-amino}-3-(5-isopropyl-thiophen-2-yl)-propionic acid methyl ester. This ester was hydrolyzed by the general procedure C to afford the title compound.

Sources & evidence

ORD record: ord-bbfcea7ed2b14a329741250ca8eee8c8
Source dataset: uspto-grants-2007_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07208601B2

Reaction notes

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