Hydrochloric Acid → 4-[(5-{3-Methyl-5-[(4-methylpyrimidin-2-yl)amino]phenyl}-1,3-thiazol-2-yl)methyl]cyclohexanecarboxylic acid

HRID 928151Notes

Reaction equation

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

Participants

Conditions

Temperature: 110 °C

Procedure

Ethyl 4-[(5-{3-methyl-5-[(4-methylpyrimidin-2-yl)amino]phenyl}-1,3-thiazol-2-yl)methyl]cyclohexanecarboxylate (147 mg, 0.326 mmol) was suspended in methanol (2.0 mL) in a microwave vial, and sodium hydroxide (1M in water, 0.652 mL, 0.652 mmol) was added. The reaction was heated to 110° C. for 30 min via microwave irradiation. The reaction was acidified to pH=3-4 with aqueous 1M HCl and extracted with 15% isopropyl alcohol in chloroform (2×). The combined organic layers were dried over magnesium sulfate and concentrated under reduced pressure to afford 4-[(5-{3-methyl-5-[(4-methylpyrimidin-2-yl)amino]phenyl}-1,3-thiazol-2-yl)methyl]cyclohexanecarboxylic acid as an off-white solid in a 2.5:1 mixture of diastereomers.

Workup

additionwas added
extractionextracted with 15% isopropyl alcohol in chloroform (2×)
dry with materialThe combined organic layers were dried over magnesium sulfate
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-876a8c962f224f76a060107a59374338
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09290490B2

Reaction notes

Loading…