Triethylamine → N-[2-(3-Amino-1-pyrrolidinyl)-6-chloro-5-quinolinyl]-cyclohexanepropanamide

HRID 2217895Notes

Reaction equation

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

Participants

Conditions

Temperature: 100 °C

Procedure

N-(2,6-Dichloro-5-quinolinyl)-cyclohexanepropanamide (Example 90(a)) (0.24 g), (S)-3-aminopyrrolidine (0.18 g) and triethylamine (0.1 mL) were suspended in acetonitrile and heated at 100° C. in a microwave for 1 hour. The resulting precipitate was filtered and then washed with acetonitrile to give a brown solid. Purification (SiO2, methanol:dichloromethane:triethylamine 3:97:0.5) gave the title compound as a colourless solid (230 mg).

Workup

filtrationThe resulting precipitate was filtered
washwashed with acetonitrile
customto give a brown solid
customPurification (SiO2, methanol:dichloromethane:triethylamine 3:97:0.5)

Sources & evidence

ORD record: ord-087eaf8028604cbf97a30287ae4175d9
Source dataset: uspto-grants-2008_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07408065B2

Reaction notes

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