Aniline → HCID 59468599, compound

HRID 1716403Notes

Reaction equation

HRID 1716403 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([C:8]2[S:12][C:11]([CH:13]=O)=[CH:10][CH:9]=2)[CH:5]=[CH:4][N:3]=1.[NH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>CC(O)=O.CC(N(C)C)=O>[Cl:1][C:2]1[N:7]=[C:6]([C:8]2[S:12][C:11]([CH2:13][NH:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)=[CH:10][CH:9]=2)[CH:5]=[CH:4][N:3]=1

Participants

5

Reactant 2

HCID 6115AnilineHCID 59857089HCID 59857089, compound

Product 1

HCID 59468599HCID 59468599, compoundYield 59.4%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 31374DimethylacetamideSolvent

Procedure

[5-(2-Chloro-pyrimidin-4-yl)-thiophene-2-carbaldehyde (100 mg, 0.446 mmol) was dissolved in 25% HOAc in DMA (4 mL) and was treated with aniline (61 uL, 0.669 mmol) for 2 h. MP-CNBH3 resin was added the reaction was shaken for 18 h. The reaction was filtered and rinsed with DMA and the solution was concentrated in vacuo. The crude material was purified by SiO2 chromatography using a gradient 0-100% hexanes/EtOAc to afford title compound (80 mg, 59%).

Workup

  1. additionMP-CNBH3 resin was added the reaction
  2. filtrationThe reaction was filtered
  3. washrinsed with DMA
  4. concentrationthe solution was concentrated in vacuo
  5. customThe crude material was purified by SiO2 chromatography

Sources & evidence

ORD record
ord-ec1fb41433be424aa496e0e49be179d2
Source dataset
uspto-grants-2010_09
Patent number
US07803806B2

Reaction notes

Loading…