1,3-Thiazol-4-ylboronic acid → HCID 66631620, compound

HRID 931816Notes

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]([C:21]1[NH:25]N=C[CH:22]=1)[CH:14]=[CH:13]2)[C:7]([OH:9])=[O:8])([CH3:4])([CH3:3])[CH3:2].[S:33]1C=C(B(O)O)N=[CH:34]1>>[C:1]([O:5][C@@H:6]([C:10]1[C:11]([C:26]2[CH:27]=[CH:28][C:29]([Cl:32])=[CH:30][CH:31]=2)=[C:12]2[C:17](=[CH:18][C:19]=1[CH3:20])[N:16]=[C:15]([C:21]1[N:25]=[CH:34][S:33][CH:22]=1)[CH:14]=[CH:13]2)[C:7]([OH:9])=[O:8])([CH3:3])([CH3:2])[CH3:4]

Participants

Reactant 2

HCID 454803181,3-Thiazol-4-ylboronic acid

HCID 66634233HCID 66634233, compound

Product 1

HCID 66631620HCID 66631620, compound

Procedure

(S)-2-tert-Butoxy-2-(5-(4-chlorophenyl)-7-methyl-2-(thiazol-4-yl)quinolin-6-yl)acetic acid (76) was prepared following the procedure 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 thiazol-4-ylboronic acid was used instead of 1H-pyrazol-5-ylboronic acid and the in the final step the reaction was stirred for 1.5 hours. 1H-NMR: 400 MHz, (CD3CN) δ: 9.07 (d, J=2.0 Hz, 1 H), 8.58 (d, J=2.0 Hz, 1 H), 8.17 (d, J=9.2 Hz, 1 H), 8.02 (s, 1 H), 7.93 (d, J=9.2 Hz, 1 H), 7.59 (m, 3 H), 7.35 (d, J=7.6 Hz, 1 H), 5.25 (s, 1H), 2.64 (s, 3 H), 0.98 (s, 9 H).

Sources & evidence

ORD record: ord-0b59cd0bd33945159db5aace733b563e
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09296758B2

Reaction notes

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