Aniline → HCID 10131444, compound

HRID 1821628Notes

Reaction equation

HRID 1821628 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([NH:9][C:10]2[N:15]=[C:14](Cl)[N:13]=[C:12]([Cl:17])[N:11]=2)=[CH:5][CH:4]=1.[NH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.C(N(C(C)C)CC)(C)C>C(#N)C>[Cl:17][C:12]1[N:11]=[C:10]([NH:9][C:6]2[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:8][CH:7]=2)[N:15]=[C:14]([NH:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[N:13]=1

Participants

5

Reactant 3

HCID 6115AnilineHCID 35312HCID 35312, compoundHCID 81531Diisopropylethylamine

Product 1

HCID 10131444HCID 10131444, compoundYield 57%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

To a solution of 2-(4-methoxyphenyl)amino-4,6-dichloro-1,3,5-triazine (57 mg, 0.21 mmoles) in acetonitrile (0.5 ml) was added a solution of aniline (0.021 ml, 0.23 mmoles) and diisopropylethylamine (0.05 ml, 0.29 mmoles) in acetonitrile (0.5 ml). After stirring for 24 hours, the mixture was concentrated under vacuum and the residue was dissolved in ethyl acetate (10 ml). The solution was washed with a solution composed of saturated aqueous sodium chloride solution and 1 M hydrochloric acid (1:1, 2×10 ml), dried over sodium sulfate, filtered, and concentrated under vacuum. The residue was purified by flash chromatography on silica gel eluting with 10% ethyl acetate-hexane to provide CT-31942 (38 mg, 57% yield). 1H NMR (d6-DMSO) δ 10.00-10.22 (m, 2H), 7.26-7.82 (m, 6H), 7.01-7.10 (m, 1H), 6.91 (d, J=9 Hz, 2H), 3.74 (s, 3H).

Workup

  1. concentrationthe mixture was concentrated under vacuum
  2. dissolutionthe residue was dissolved in ethyl acetate (10 ml)
  3. washThe solution was washed with a solution
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under vacuum
  7. customThe residue was purified by flash chromatography on silica gel eluting with 10% ethyl acetate-hexane
  8. customto provide CT-31942 (38 mg, 57% yield)

Sources & evidence

ORD record
ord-56c1918d953f4382a7a006b1b5551073
Source dataset
uspto-grants-2009_10
Patent number
US07608620B2

Reaction notes

Loading…