Phosphorus oxychloride → HCID 90022223, compound

HRID 1754845Notes

Reaction equation

HRID 1754845 reaction equation
[CH2:1]([O:3][C:4](=[O:27])[CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([Cl:13])=[CH:9][C:8]=1[C:14](=O)[NH:15][CH2:16][CH2:17][C:18]1[N:19]=[C:20]([CH:23]([CH3:25])[CH3:24])[S:21][CH:22]=1)[CH3:2].O=P(Cl)(Cl)Cl>CC#N>[Cl:13][C:10]1[CH:11]=[CH:12][C:7]([O:6][CH2:5][C:4]([O:3][CH2:1][CH3:2])=[O:27])=[C:8]([C:14]2[C:22]3[S:21][C:20]([CH:23]([CH3:25])[CH3:24])=[N:19][C:18]=3[CH2:17][CH2:16][N:15]=2)[CH:9]=1

Participants

4

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 90022701HCID 90022701, compound

Product 1

HCID 90022223HCID 90022223, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of {4-chloro-2-[2-(2-isopropyl-thiazol-4-yl)-ethylcarbamoyl]-phenoxy}-acetic acid ethyl ester (100 mg, 0.24 mmol, 1 eq.) and POCl3 (0.34 mL, 3.65 mmol, 15 eq.) in MeCN (2 mL) was stirred at 80° C. for 18 hours. The mixture was allowed to cool down to r.t. and concentrated in vacuo. The residue was purified by prep. HPLC (column: Atlantis, 30×75 mm, 10 um, UV/MS, acidic conditions) and concentrated in vacuo to give ethyl 2-(4-chloro-2-(2-isopropyl-6,7-dihydrothiazolo[5,4-c]pyridin-4-yl)phenoxy)acetate as a yellow oil.

Workup

  1. temperatureto cool down to r.t.
  2. concentrationconcentrated in vacuo
  3. customThe residue was purified by prep
  4. concentrationHPLC (column: Atlantis, 30×75 mm, 10 um, UV/MS, acidic conditions) and concentrated in vacuo

Sources & evidence

ORD record
ord-07c43516a5154f56863868611d69ae62
Source dataset
uspto-grants-2015_10
Patent number
US09169270B2

Reaction notes

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