Cyclohexylamine → HCID 57829849, compound

HRID 1855431Notes

Reaction equation

HRID 1855431 reaction equation
Cl[C:2]1[CH:7]=[C:6]([CH3:8])[N:5]=[C:4]([NH:9][C:10]2[CH:15]=[CH:14][C:13]([N:16]3[CH:20]=[C:19]([CH3:21])[N:18]=[CH:17]3)=[C:12]([O:22][CH3:23])[CH:11]=2)[N:3]=1.[CH:24]1([NH2:30])[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]1>CN1C=CC(=O)C1=O>[CH:24]1([NH:30][C:2]2[CH:7]=[C:6]([CH3:8])[N:5]=[C:4]([NH:9][C:10]3[CH:15]=[CH:14][C:13]([N:16]4[CH:20]=[C:19]([CH3:21])[N:18]=[CH:17]4)=[C:12]([O:22][CH3:23])[CH:11]=3)[N:3]=2)[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]1

Participants

4

Reactant 2

HCID 7965Cyclohexylamine2×HCID 57829826HCID 57829826, compound

Product 1

HCID 57829849HCID 57829849, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 21908797HCID 21908797, compoundSolvent

Procedure

A solution of (4-chloro-6-methyl-pyrimidin-2-yl)-[3-methoxy-4-(4-methyl-imidazol-1-yl)-phenyl]-amine (66 mg, 0.2 mmol) and cyclohexylamine (60 mg, 0.6 mmol) in N-methylpyrroldione (2 mL) was heated for 30 min to 200° C. in a microwave oven. Additional cyclohexylamine (60 mg, 0.6 mmol) was added and the reaction was heated for 30 min to 200° C. in a microwave oven. The reaction mixture was poured onto water and the precipitate was filtered off, washed with water, dissolved in 1N aqueous sodium hydroxide solution and extracted twice with diethyl ether. The combined organic layers were washed with water, once with brine, dried over sodium sulfate, filtered and the solvent was evaporated under reduced pressure to yield the title compound as a light brown solid (64 mg, 82%). MS ISP (m/e): 393.4 (100) [(M+H)+]. 1H NMR (CDCl3, 300 MHz): δ (ppm)=7.60 (br s, 2H), 7.13 (s, 2H), 6.92 (br s, 1H), 6.86 (s, 1H), 5.75 (s, 1H), 4.61 (m, 1H), 3.85 (s, 3H), 3.69 (m, 1H), 2.30 (s, 3H), 2.26 (s, 3H), 2.05 (br d, 2H), 1.60-1.82 (m, 4H), 1.18-1.45 (m, 4H).

Workup

  1. temperaturethe reaction was heated for 30 min to 200° C. in a microwave oven
  2. additionThe reaction mixture was poured onto water
  3. filtrationthe precipitate was filtered off
  4. washwashed with water
  5. dissolutiondissolved in 1N aqueous sodium hydroxide solution
  6. extractionextracted twice with diethyl ether
  7. washThe combined organic layers were washed with water, once with brine
  8. dry with materialdried over sodium sulfate
  9. filtrationfiltered
  10. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-6434b64e5daa4f1ab5dd9a2f52703049
Source dataset
uspto-grants-2015_02
Patent number
US08962834B2

Reaction notes

Loading…