Chloroacetaldehyde → [3-(2-Methoxy-ethoxy)-5-phenoxy-pyridine-2-yl]-thiazole-2-yl-amine

HRID 1966219Notes

Reaction equation

[CH3:1][O:2][CH2:3][CH2:4][O:5][C:6]1[C:7]([NH:19][C:20]([NH2:22])=[S:21])=[N:8][CH:9]=[C:10]([O:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:11]=1.Cl[CH2:24][CH:25]=O>CN(C=O)C>[CH3:1][O:2][CH2:3][CH2:4][O:5][C:6]1[C:7]([NH:19][C:20]2[S:21][CH:24]=[CH:25][N:22]=2)=[N:8][CH:9]=[C:10]([O:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:11]=1

Participants

Conditions

Temperature: 100 °C

Procedure

[3-(2-Methoxy-ethoxy)-5-phenoxy-pyridine-2-yl]-thiourea (0.24 mmol) is dissolved in DMF (1 ml) and chloro-acetaldehyde (1.1 eq., 55% in water) is added and stirred 3 hours at 100° C. After cooling to room temperature the suspension is pored into ice-water and extracted with methyl-tert.-butyl ether. The combined organic phases are washed with brine and dried over MgSO4. The solvent is removed in vacuo. [3-(2-Methoxy-ethoxy)-5-phenoxy-pyridine-2-yl]-thiazole-2-yl-amine (“A20”) is obtained after reversed phase chromatography (water/acetonitrile 0.1% TFA) as yellow solid in a yield of 45%; mp. 140.6-140.9°; HPLC (method C): 1.73 min; LC-MS (method A): 1.589 min, 344.1 (M+H+);

Workup

temperatureAfter cooling to room temperature the suspension
extractionextracted with methyl-tert.-butyl ether
washThe combined organic phases are washed with brine
dry with materialdried over MgSO4
customThe solvent is removed in vacuo

Sources & evidence

ORD record: ord-671bc1aec39b4c12893403b526887add
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08420642B2

Reaction notes

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