Isopropyl isocyanate → 1-[2-((R)-Indan-1-ylamino)-quinolin-6-yl]-3-isopropyl-urea

HRID 1928712Notes

Reaction equation

HRID 1928712 reaction equation
[C@H:1]1([NH:10][C:11]2[CH:20]=[CH:19][C:18]3[C:13](=[CH:14][CH:15]=[C:16]([NH2:21])[CH:17]=3)[N:12]=2)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH2:2]1.[CH:22]([N:25]=[C:26]=[O:27])([CH3:24])[CH3:23]>C1(C)C=CC=CC=1>[C@H:1]1([NH:10][C:11]2[CH:20]=[CH:19][C:18]3[C:13](=[CH:14][CH:15]=[C:16]([NH:21][C:26]([NH:25][CH:22]([CH3:24])[CH3:23])=[O:27])[CH:17]=3)[N:12]=2)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 61277Isopropyl isocyanateHCID 57860958(R)-N2-Indan-1-yl-quinoline-2,6-diamine

Product 1

HCID 442173041-[2-((R)-Indan-1-ylamino)-quinolin-6-yl]-3-isopropyl-ureaYield 85%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
60 °C

Procedure

(R)—N2-Indan-1-yl-quinoline-2,6-diamine (0.30 g, 1.09 mmol) was dissolved in toluene (5 mL). Isopropyl isocyanate (0.93 g, 1.09 mmol) was added and the reaction mixture was stirred at 60° C. for 2 h. Upon cooling to room temperature a precipitation formed which was filtered off and washed twice with dichloromethane. After drying the title compound was obtained as a white solid (330 mg, 85%); MS: m/e=276.4 (M+H+).

Workup

  1. temperatureUpon cooling to room temperature
  2. customa precipitation
  3. customformed which
  4. filtrationwas filtered off
  5. washwashed twice with dichloromethane
  6. dry with materialAfter drying the title compound

Sources & evidence

ORD record
ord-5e74e329486a4d69b8d73572d8ba855d
Source dataset
uspto-grants-2012_05
Patent number
US08183380B2

Reaction notes

Loading…