Methoxyacetic Acid → N-(4-{2-[(5-isopropyl-1,3-thiazol-2-yl)amino]-2-oxoethyl}phenyl)-2-methoxyacetamide

HRID 1837609Notes

Reaction equation

HRID 1837609 reaction equation
[CH3:1][O:2][CH2:3][C:4]([OH:6])=O.[NH2:7][C:8]1[CH:13]=[CH:12][C:11]([CH2:14][C:15]([NH:17][C:18]2[S:19][C:20]([CH:23]([CH3:25])[CH3:24])=[CH:21][N:22]=2)=[O:16])=[CH:10][CH:9]=1>C(Cl)Cl.C1(N=C=N)CCCCC1.CN(C1C=CN=CC=1)C.C(Cl)Cl.CN(C=O)C>[CH:23]([C:20]1[S:19][C:18]([NH:17][C:15](=[O:16])[CH2:14][C:11]2[CH:10]=[CH:9][C:8]([NH:7][C:4](=[O:6])[CH2:3][O:2][CH3:1])=[CH:13][CH:12]=2)=[N:22][CH:21]=1)([CH3:25])[CH3:24]

Participants

7

Reactant 2

HCID 12251Methoxyacetic AcidHCID 221707522-(4-aminophenyl)-N-(5-isopropyl-1,3-thiazol-2-yl)acetamide

Product 1

HCID 11405288N-(4-{2-[(5-isopropyl-1,3-thiazol-2-yl)amino]-2-oxoethyl}phenyl)-2-methoxyacetamide

Reagents, catalysts & solvents 4

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×HCID 12048208N-CyclohexylcarbodiimideSolventHCID 22350042dichloromethane N,N-dimethylformamideSolvent

Procedure

To a solution of 2-methoxyacetic acid (41 μl, 0.53 mmol) in CH2Cl2 (1.5 ml), N-cyclohexylcarbodiimide, N′-methyl polystyrene (0.53 g, loading 2 mmol/g, 1.064 mmol), previously washed with CH2Cl2 (5 ml×3), 4-DMAP (0.032 g, 0.266 mmol) and a solution of 2-(4-aminophenyl)-N-(5-isopropyl-1,3-thiazol-2-yl)acetamide (0.076 g, 0.266 mmol) in CH2Cl2/DMF (0.4 ml/10.6 ml) were added. The reaction mixture was maintained under stirring at room temperature for about 72 hours the resin was filtered, washed with CH2Cl2 (10 ml×3), the filtrated combined, washed with water, 5% hydrochloric acid, water, saturated sodium bicarbonate and water, dried and evaporated.

Workup

  1. temperatureThe reaction mixture was maintained
  2. filtrationwas filtered
  3. washwashed with CH2Cl2 (10 ml×3)
  4. washwashed with water, 5% hydrochloric acid, water, saturated sodium bicarbonate and water
  5. customdried
  6. customevaporated

Sources & evidence

ORD record
ord-3a9f2f0b1da24de7b62f5663aa64d38d
Source dataset
uspto-grants-2004_08
Patent number
US06784198B1

Reaction notes

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