HCID 53733769, compound → HCID 54543763, compound

HRID 1066504Notes

Reaction equation

C([O:8][C:9]1[CH:10]=[C:11]([C:15]2[N:20]=[C:19]([NH:21][S:22]([C:25]3[S:26][C:27]([CH3:30])=[CH:28][N:29]=3)(=[O:24])=[O:23])[C:18]([O:31][C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][C:33]=3[O:38][CH3:39])=[C:17]([O:40][CH3:41])[N:16]=2)[CH:12]=[CH:13][CH:14]=1)C1C=CC=CC=1>C(Cl)Cl.Cl[Ti](Cl)(Cl)Cl>[OH:8][C:9]1[CH:10]=[C:11]([C:15]2[N:20]=[C:19]([NH:21][S:22]([C:25]3[S:26][C:27]([CH3:30])=[CH:28][N:29]=3)(=[O:24])=[O:23])[C:18]([O:31][C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][C:33]=3[O:38][CH3:39])=[C:17]([O:40][CH3:41])[N:16]=2)[CH:12]=[CH:13][CH:14]=1

Participants

Conditions

Temperature: 0 °C

Procedure

A solution of 0.35 g of 5-methyl-thiazole-2-sulfonic acid [2-(3-benzyloxy-phenyl)-6-methoxy-5-(2-methoxy-phenoxy)-pyrimidin-4-yl]-amide dissolved in CH2Cl2 (40 ml) is cooled to 0° C. and treated dropwise with 4.8 ml of a 1M solution of TiCl4 in CH2Cl2. The orange solution is stirred at 0° C. for 0.5 h until the starting material was consumed according to TLC analysis (Me2Cl2/EtOAc: 4/1). The reaction solution was then poured on ice, the product extracted into Me2Cl2 the organic layer dried over Na2SO4 and the solvent removed in vacuo. The residue was washed with ether/hexane to give 5-methyl-thiazole-2-sulfonic acid [2-(3-hydroxy-phenyl)-6-methoxy-5-(2-methoxy-phenoxy)-pyrimidin-4-yl]-amide as an off-white crystalline solid. ISN mass spectrum, m/e 499.1 (M−1 calculated for C22H20N4O6S2: 499).

Workup

customwas consumed
additionThe reaction solution was then poured on ice
extractionthe product extracted into Me2Cl2 the organic layer
dry with materialdried over Na2SO4
customthe solvent removed in vacuo
washThe residue was washed with ether/hexane

Sources & evidence

ORD record: ord-06aced7d75ef4924be59c7fb8ba917c9
Source dataset: uspto-grants-2001_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06242601B1

Reaction notes

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