Methanol → HCID 58289508, compound

HRID 1422540Notes

Reaction equation

[CH3:1][O:2][CH:3]([O:26][CH3:27])[CH2:4][O:5][C:6]1[C:15]([CH3:16])=[C:14]2[C:9]([C:10](O)=[CH:11][C:12]([C:17]3[S:18][CH:19]=[C:20]([CH:22]([CH3:24])[CH3:23])[N:21]=3)=[N:13]2)=[CH:8][CH:7]=1.O=P(Cl)(Cl)[Cl:30].CO.C(=O)(O)[O-].[Na+]>N1C=CC=CC=1>[Cl:30][C:10]1[C:9]2[C:14](=[C:15]([CH3:16])[C:6]([O:5][CH2:4][CH:3]([O:26][CH3:27])[O:2][CH3:1])=[CH:7][CH:8]=2)[N:13]=[C:12]([C:17]2[S:18][CH:19]=[C:20]([CH:22]([CH3:24])[CH3:23])[N:21]=2)[CH:11]=1

Participants

Conditions

Temperature: 80 °C

Procedure

7-(2,2-Dimethoxy-ethoxy)-2-(4-isopropyl-thiazol-2-yl)-8-methyl-quinolin-4-ol (875 mg, 2.3 mmol) was dissolved in pyridine (20 mL). POCl3 (4.2 ml, 46.0 mmol) was added slowly. The reaction was heated at 80° C. for 4 hours. The reaction was cooled to 0° C. and methanol (5 mL) was added. The reaction was neutralized with a saturated aqueous sodium bicarbonate solution. The product was extracted with ethyl acetate (3×20 mL). The combined organics were dried with sodium sulfate, filtered and was concentrated. 4-Chloro-7-(2,2-dimethoxy-ethoxy)-2-(4-isopropyl-thiazol-2-yl)-8-methyl-quinoline (410 mg, 44%) was purified by silica gel chromatography.

Workup

temperatureThe reaction was cooled to 0° C.
extractionThe product was extracted with ethyl acetate (3×20 mL)
dry with materialThe combined organics were dried with sodium sulfate
filtrationfiltered
concentrationwas concentrated
custom4-Chloro-7-(2,2-dimethoxy-ethoxy)-2-(4-isopropyl-thiazol-2-yl)-8-methyl-quinoline (410 mg, 44%) was purified by silica gel chromatography

Sources & evidence

ORD record: ord-2afc8eddc93d4930a71724e0cf0d44c9
Source dataset: uspto-grants-2015_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08927484B2

Reaction notes

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