(3S)-(-)-3-Aminopyrrolidine → 2-[(3S)-3-Amino-1-pyrrolidinyl]-6-chloro-N-(cyclohexylmethyl)-5-quinolinecarboxamide

HRID 2217842Notes

Reaction equation

Cl[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>[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

Conditions

Temperature: 100 °C

Procedure

A stirred suspension of 2,6-dichloro-N-(cyclohexylmethyl)quinoline-5-carboxamide (Example 43(a)) (500 mg) and (3S)-3-pyrrolidinamine (0.60 mL) in acetonitrile (3 mL) was heated at 100° C. in a microwave for 40 minutes after which it was cooled to room temperature and concentrated. Purification by chromatography (SiO2, dichloromethane:methanol:ammonia in methanol (7 M) 95:5:0.5 as eluant) and subsequent recrystallisation (acetonitrile) afforded the title compound as a solid (280 mg).

Workup

temperaturewas cooled to room temperature
concentrationconcentrated
customPurification
customby chromatography (SiO2, dichloromethane:methanol:ammonia in methanol (7 M) 95:5:0.5 as eluant) and subsequent recrystallisation (acetonitrile)

Sources & evidence

ORD record: ord-02a9fc8d6e88466f829558b7d53a102e
Source dataset: uspto-grants-2008_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07408065B2

Reaction notes

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