Pyrrolidine → HCID 22641468, compound

HRID 2415486Notes

Reaction equation

HRID 2415486 reaction equation
[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:12][CH3:13])=[CH:9][CH:10]=2)[N:5]=[C:4]([NH2:14])[CH:3]=1.[NH:15]1[CH2:19][CH2:18][CH2:17][CH2:16]1>C(O)(C)C>[ClH:1].[CH3:13][O:12][C:8]1[CH:7]=[C:6]2[C:11]([C:2]([N:15]3[CH2:19][CH2:18][CH2:17][CH2:16]3)=[CH:3][C:4]([NH2:14])=[N:5]2)=[CH:10][CH:9]=1

Participants

4

Reactant 2

HCID 31268PyrrolidineHCID 14067409HCID 14067409, compound

Product 1

HCID 22641468HCID 22641468, compoundYield 21%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
60 °C

Procedure

A solution of 319 mg (0.92 mmol) of 4-chloro-7-methoxy-quinolin-2-ylamine in 20 ml of isopropanol was treated with 130 mg (1.83 mmol) of pyrrolidine and heated at 60° C. for 6 h. The reaction mixture was cooled to RT, concentrated in vacuo. The residue was applied to a silica gel column with hexane/AcOEt (1:1) as eluent. The purified fractions were combined and concentrated in vacuo upon which the desired product crystallized out. The crystals were filtered off and dried in a high vacuum to give 48 mg (21%) of 7-methoxy-4-pyrrolidin-1-yl-quinolin-2-ylamine hydrochloride as a light brown solid. EI mass spectrum, m/e: 243.2 (M calculated for C14H17N3O: 243).

Workup

  1. temperatureThe reaction mixture was cooled to RT
  2. concentrationconcentrated in vacuo
  3. concentrationconcentrated in vacuo upon which the desired product
  4. customcrystallized out
  5. filtrationThe crystals were filtered off
  6. customdried in a high vacuum

Sources & evidence

ORD record
ord-318690c4ed104725b68a60b5535f62f2
Source dataset
uspto-grants-2004_11
Patent number
US06818767B2

Reaction notes

Loading…