Reaction equation
Cl.C([O:4][C:5](=[O:24])[CH2:6][O:7][C:8]1[CH:13]=[CH:12][C:11]([Cl:14])=[CH:10][C:9]=1[CH:15]1[C:20]2[S:21][CH:22]=[N:23][C:19]=2[CH2:18][CH2:17][NH:16]1)C.CCN(CC)CC.[CH3:32][O:33][C:34]1[CH:43]=[CH:42][CH:41]=[CH:40][C:35]=1[CH2:36][N:37]=[C:38]=[S:39].[OH-].[Na+]>CC#N.C(O)=O>[Cl:14][C:11]1[CH:12]=[CH:13][C:8]([O:7][CH2:6][C:5]([OH:4])=[O:24])=[C:9]([CH:15]2[C:20]3[S:21][CH:22]=[N:23][C:19]=3[CH2:18][CH2:17][N:16]2[C:38](=[S:39])[NH:37][CH2:36][C:35]2[CH:40]=[CH:41][CH:42]=[CH:43][C:34]=2[O:33][CH3:32])[CH:10]=1Participants
7
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Procedure
To a solution of (±)-[4-chloro-2-(4,5,6,7-tetrahydro-thiazolo[5,4-c]pyridin-4-yl)-phenoxy]-acetic acid ethyl ester hydrochloride (50 mg, 0.13 mmol, 1.00 eq.) and NEt3 (54 μL, 0.39 mmol, 3.00 eq.) in MeCN (1 mL), 2-methoxybenzyl isothiocyanate (24 mg, 0.14 mmol, 1.05 eq.) in MeCN (1 mL) was added. The mixture was stirred at r.t. for 18 hours. 1M aq. NaOH (0.5 mL) was added. The mixture was stirred at r.t. for 18 hours. The solution was neutralized with formic acid, purified by prep. HPLC (column: Atlantis, 30×75 mm, 10 um, UV/MS, acidic conditions), and concentrated in vacuo to give the desired acid as a white solid.
Workup
- stirringThe mixture was stirred at r.t. for 18 hours
- custompurified by prep
- concentrationHPLC (column: Atlantis, 30×75 mm, 10 um, UV/MS, acidic conditions), and concentrated in vacuo
Sources & evidence
- ORD record
- ord-c0b01d7c0be74736aacdc50b232042f4
- Source dataset
- uspto-grants-2015_10
- Patent number
- US09169270B2
Linked notes
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