(3R)-pyrrolidin-3-amine → HCID 68810722, compound

HRID 2217845Notes

Reaction equation

HRID 2217845 reaction equation
[Cl:1][C:2]1[CH:11]=[CH:10][C:9]2[C:8]([C:12]([NH:14][CH2:15][CH:16]3[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]3)=[O:13])=[C:7]([Cl:22])[CH:6]=[CH:5][C:4]=2[N:3]=1.[NH:23]1[CH2:27][CH2:26][C@@H:25]([NH2:28])[CH2:24]1>C(#N)C>[ClH:1].[ClH:1].[NH2:28][C@@H:25]1[CH2:26][CH2:27][N:23]([C:2]2[CH:11]=[CH:10][C:9]3[C:8]([C:12]([NH:14][CH2:15][CH:16]4[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]4)=[O:13])=[C:7]([Cl:22])[CH:6]=[CH:5][C:4]=3[N:3]=2)[CH2:24]1

Participants

4

Reactant 2

HCID 1519352(3R)-pyrrolidin-3-amineHCID 860130222,6-dichloro-N-(cyclohexylmethyl)-5-quinolinecarboxamide

Product 1

HCID 68810722HCID 68810722, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
100 °C

Procedure

A stirred suspension of 2,6-dichloro-N-(cyclohexylmethyl)quinoline-5-carboxamide (Example 43(a)) (200 mg) and (3R)-3-pyrrolidinamine (0.20 mL) in acetonitrile (2 mL) was heated at 100° C. in a microwave for 1 hour after which it was cooled to room temperature and concentrated. The residue was purified by chromatography (SiO2, dichloromethane:methanol:ammonia in methanol (7 M) (95:5:1), and then by HPLC (Symmetry—0.1% aqueous trifluoroacetic acid/acetonitrile). Conversion to the dihydrochloride salt by treatment with hydrochloric acid (4M in 1,4-dioxane) and subsequent recrystallisation (methanol/ethyl acetate) afforded the title compound as a solid (46 mg).

Workup

  1. temperaturewas cooled to room temperature
  2. concentrationconcentrated
  3. customThe residue was purified by chromatography (SiO2, dichloromethane
  4. customConversion to the dihydrochloride salt by treatment with hydrochloric acid (4M in 1,4-dioxane) and subsequent recrystallisation (methanol/ethyl acetate)

Sources & evidence

ORD record
ord-059143402f1848579ac10406899ee42d
Source dataset
uspto-grants-2008_08
Patent number
US07408065B2

Reaction notes

Loading…