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

HRID 2217825Notes

Reaction equation

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

Participants

Conditions

Temperature: 100 °C

Procedure

To a 10 mL vial was added N-(2,6-dichloro-5-quinolinyl)-cyclohexaneacetamide (Example 1(a)) (0.166 g), (3R)-3-pyrrolidinamine (0.127 g), triethylamine (0.083 mL) and acetonitrile (5 mL). The vial was sealed and heated at 100° C. for 30 minutes within a microwave. The reaction was cooled to room temperature and the resulting solid removed by filtration. This solid was purified (Varian SCX cartridge, using methanol and 10% ammonia in methanol as eluant) to afford the title compound (0.102 g).

Workup

customThe vial was sealed
temperatureThe reaction was cooled to room temperature
customthe resulting solid removed by filtration
customThis solid was purified (Varian SCX cartridge, using methanol and 10% ammonia in methanol as eluant)

Sources & evidence

ORD record: ord-d6c00237a8fe4fa6a7c979b0bb6a3376
Source dataset: uspto-grants-2008_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07408065B2

Reaction notes

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