(Pyrimidin-5-yl)boronic acid → HCID 66631458, compound

HRID 931820Notes

Reaction equation

[C:1]([O:5][C@@H:6]([C:10]1[C:11]([C:26]2[CH:31]=[CH:30][C:29]([Cl:32])=[CH:28][CH:27]=2)=[C:12]2[C:17](=[CH:18][C:19]=1[CH3:20])[N:16]=[C:15](C1NN=CC=1)[CH:14]=[CH:13]2)[C:7]([OH:9])=[O:8])([CH3:4])([CH3:3])[CH3:2].[N:33]1[CH:38]=[C:37](B(O)O)[CH:36]=[N:35][CH:34]=1>>[C:1]([O:5][C@@H:6]([C:10]1[C:11]([C:26]2[CH:31]=[CH:30][C:29]([Cl:32])=[CH:28][CH:27]=2)=[C:12]2[C:17](=[CH:18][C:19]=1[CH3:20])[N:16]=[C:15]([C:37]1[CH:38]=[N:33][CH:34]=[N:35][CH:36]=1)[CH:14]=[CH:13]2)[C:7]([OH:9])=[O:8])([CH3:3])([CH3:2])[CH3:4]

Participants

Reactant 2

HCID 2795193(Pyrimidin-5-yl)boronic acid

HCID 66634233HCID 66634233, compound

Product 1

HCID 66631458HCID 66631458, compound

Procedure

(S)-2-tert-Butoxy-2-(5-(4-chlorophenyl)-7-methyl-2-(pyrimidin-5-yl)quinolin-6-yl)acetic acid (87) was prepared following the procedure used for (S)-2-tert-butoxy-2-(5-(4-chlorophenyl)-7-methyl-2-(1H-pyrazol-5-yl)quinolin-6-yl)acetic acid of Example 70 except that pyrimidin-5-ylboronic acid was used instead of 1H-pyrazol-5-ylboronic acid. 1H-NMR: 400 MHz, (CD3CN) δ: 9.52 (br s, 2 H), 9.26 (s, 1 H), 8.00 (s, 1H), 7.90 (d, J=8.8 Hz, 1 H), 7.83 (d, J=9.2 Hz, 1 H), 7.60 (m, 3 H), 7.37 (d, J=7.6 Hz, 1 H), 5.27 (s, 1 H), 2.65 9s, 3 H), 0.99 (s, 9 H). LCMS-ESI+ (m/z): [M+H]+ calcd for C26H25ClN3O3: 462.15. found: 462.45.

Sources & evidence

ORD record: ord-400e78d802554635af8613d92d172863
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09296758B2

Reaction notes

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