Chloroacetaldehyde → HCID 25261177, compound

HRID 1966224Notes

Reaction equation

HRID 1966224 reaction equation
[CH:1]1([O:6][C:7]2[C:8]([NH:20][C:21]([NH2:23])=[S:22])=[N:9][CH:10]=[C:11]([O:13][C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[CH:12]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.Cl[CH2:25][CH:26]=O>CN(C=O)C>[CH:1]1([O:6][C:7]2[C:8]([NH:20][C:21]3[S:22][CH:25]=[CH:26][N:23]=3)=[N:9][CH:10]=[C:11]([O:13][C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=3)[CH:12]=2)[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

4

Reactant 2

HCID 33ChloroacetaldehydeHCID 86644603HCID 86644603, compound

Product 1

HCID 25261177HCID 25261177, compoundYield 47%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

(3-Cyclopentyloxy-5-phenoxy-pyridine-2-yl)-thiourea (0.29 mmol) is dissolved in DMF (1 ml) and chloro-acetaldehyde (1.1 eq., 55% in water) is added and stirred 3 h at 100° C. After cooling to room temperature the suspension is pored into ice-water and extracted with methyl-ter.-butyl ether. The combined organic phases are washed with brine and dried over MgSO4. The solvent is removed in vacuo. (3-Cyclopentyloxy-5-phenoxy-pyridine-2-yl)-thiazole-2-yl-amine (“A21”) is obtained after reversed phase chromatography (water/acetonitrile+0.1% TFA) as yellow solid in a yield of 47%; 138.2-139.7°; HPLC (method C): 2.00 min; LC-MS (method A): 2.00 min, 354.1 (M+H+);

Workup

  1. temperatureAfter cooling to room temperature the suspension
  2. extractionextracted with methyl-ter
  3. washThe combined organic phases are washed with brine
  4. dry with materialdried over MgSO4
  5. customThe solvent is removed in vacuo

Sources & evidence

ORD record
ord-fc46fee2bab34a6f9e21fcd534eacf75
Source dataset
uspto-grants-2013_04
Patent number
US08420642B2

Reaction notes

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