Pyridine → 2-Chloro-N-{4-methyl-5-[2-(3-nitro-phenylamino)-pyrimidin-4-yl]-thiazol-2-yl}-acetamide

HRID 599144Notes

Reaction equation

HRID 599144 reaction equation
[NH2:1][C:2]1[S:3][C:4]([C:8]2[CH:13]=[CH:12][N:11]=[C:10]([NH:14][C:15]3[CH:20]=[CH:19][CH:18]=[C:17]([N+:21]([O-:23])=[O:22])[CH:16]=3)[N:9]=2)=[C:5]([CH3:7])[N:6]=1.[Cl:24][CH2:25][C:26](Cl)=[O:27].N1C=CC=CC=1>CN(C=O)C>[Cl:24][CH2:25][C:26]([NH:1][C:2]1[S:3][C:4]([C:8]2[CH:13]=[CH:12][N:11]=[C:10]([NH:14][C:15]3[CH:20]=[CH:19][CH:18]=[C:17]([N+:21]([O-:23])=[O:22])[CH:16]=3)[N:9]=2)=[C:5]([CH3:7])[N:6]=1)=[O:27]

Participants

5

Reactant 3

HCID 1049PyridineHCID 6577Chloroacetyl chlorideHCID 4479614-(2-Amino-4-methyl-5-thiazolyl)-N-(3-nitrophenyl)-2-pyrimidinamine

Product 1

HCID 101793942-Chloro-N-{4-methyl-5-[2-(3-nitro-phenylamino)-pyrimidin-4-yl]-thiazol-2-yl}-acetamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of [4-(2-amino-4-methyl-thiazol-5-yl)-pyrimidin-2-yl]-(3-nitro-phenyl)-amine (0.33 g, 1.0 mmol,) in dry DMF (3 mL) was cooled on an ice-water bath. Chloroacetyl chloride (0.22 g, 2.0 mmol) and pyridine (80 μL) were added. After stirring at room temperature for 18 h, the reaction mixture was concentrated, poured into ice water and extracted with CH2Cl2. The organic phases were combined, washed with brine, dried on MgSO4 and evaporated to dryness. The resulting greenish residue was purified by SiO2 chromatography (1:1 EtOAc/PE) to afford the title compound as a gray solid. Anal. RP-HPLC: tR=20.6 min (0-60% MeCN in 0.1% aq CF3COOH over 20 min, 1 mL/min, purity >97%). 1H-NMR (DMSO-d6) δ: 2.45 (s, 3H, CH3), 4.12 (s, 2H, CH2), 7.03 (d, 1H, J=5.2 Hz, pyrimidinyl-H), 7.42 (m, 1H, Ph-H), 7.63 (m, 1H, Ph-H), 8.01 (m, 1H, Ph-H), 8.41 (d, 1H, J=5.2 Hz, pyrimidinyl-H), 8.64 (s, 1H, Ph-H).

Workup

  1. concentrationthe reaction mixture was concentrated
  2. additionpoured into ice water
  3. extractionextracted with CH2Cl2
  4. washwashed with brine
  5. customdried on MgSO4
  6. customevaporated to dryness
  7. customThe resulting greenish residue was purified by SiO2 chromatography (1:1 EtOAc/PE)

Sources & evidence

ORD record
ord-b29e97d61572420886a31647d40b7df9
Source dataset
uspto-grants-2011_03
Patent number
US07897605B2

Reaction notes

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