Water → N-(5-Chloro-2-methylphenyl)-4-{4-[5-(2-formylphenyl)-4,5-dihydro-1,2-oxazol-3-yl]-1,3-thiazol-2-yl}piperidine-1-carboxamide

HRID 1747252Notes

Reaction equation

HRID 1747252 reaction equation
Cl.[NH:2]1[CH2:7][CH2:6][CH:5]([C:8]2[S:9][CH:10]=[C:11]([C:13]3[CH2:17][CH:16]([C:18]4[CH:25]=[CH:24][CH:23]=[CH:22][C:19]=4[CH:20]=[O:21])[O:15][N:14]=3)[N:12]=2)[CH2:4][CH2:3]1.[Cl:26][C:27]1[CH:32]=[CH:31][C:30]([CH3:33])=[C:29]([N:34]=[C:35]=[O:36])[CH:28]=1.O>ClCCl.C(N(C(C)C)CC)(C)C.N12CCCN=C1CCCCC2>[Cl:26][C:27]1[CH:32]=[CH:31][C:30]([CH3:33])=[C:29]([NH:34][C:35]([N:2]2[CH2:3][CH2:4][CH:5]([C:8]3[S:9][CH:10]=[C:11]([C:13]4[CH2:17][CH:16]([C:18]5[CH:25]=[CH:24][CH:23]=[CH:22][C:19]=5[CH:20]=[O:21])[O:15][N:14]=4)[N:12]=3)[CH2:6][CH2:7]2)=[O:36])[CH:28]=1

Participants

7

Reactant 3

HCID 962WaterHCID 27696325-Chloro-2-methylphenyl isocyanateHCID 866652252-{3-[2-(Piperidin-4-yl)-1,3-thiazol-4-yl]-4,5-dihydro-1,2-oxazol-5-yl}benzaldehyde hydrochloride

Product 1

HCID 86665224N-(5-Chloro-2-methylphenyl)-4-{4-[5-(2-formylphenyl)-4,5-dihydro-1,2-oxazol-3-yl]-1,3-thiazol-2-yl}piperidine-1-carboxamide

Reagents, catalysts & solvents 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneCatalystHCID 6344DichloromethaneSolventHCID 81531DiisopropylethylamineSolvent

Procedure

To a suspension of 2-{3-[2-(piperidin-4-yl)-1,3-thiazol-4-yl]-4,5-dihydro-1,2-oxazol-5-yl}benzaldehyde hydrochloride (1.43 g) in dichloromethane (30 ml) and diisopropylethylamine (0.73 ml) were added, at room temperature, 4-chloro-2-isocyanato-1-methylbenzene (700 mg) and one drop of 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU). The mixture was stirred at room temperature overnight, and water was then added. The aqueous phase was removed and extracted with ethyl acetate. The combined organic phases were dried over sodium sulphate and concentrated under reduced pressure. The residue was purified by chromatography. This gave N-(5-chloro-2-methylphenyl)-4-{4-[5-(2-formylphenyl)-4,5-dihydro-1,2-oxazol-3-yl]-1,3-thiazol-2-yl}piperidine-1-carboxamide (1.23 g).

Workup

  1. additionwere added, at room temperature
  2. customThe aqueous phase was removed
  3. extractionextracted with ethyl acetate
  4. dry with materialThe combined organic phases were dried over sodium sulphate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by chromatography

Sources & evidence

ORD record
ord-da50be54f4bb422faf2c5dbd7b1b2119
Source dataset
uspto-grants-2015_10
Patent number
US09150565B2

Reaction notes

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