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

HRID 2217856Notes

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[CH2:28][CH2:27][CH2:26][C@H:25]([NH2:29])[CH2:24]1.C(N(CC)CC)C>C(#N)C>[NH2:29][C@H:25]1[CH2:26][CH2:27][CH2:28][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: 120 °C

Procedure

N-(2,6-Dichloro-5-quinolinyl)-cyclohexaneacetamide (Example 1(a)) (0.2 g), (3S)-3-piperidinamine (0.089 g) and triethylamine (0.25 mL) were placed into a 10 mL microwave vial followed by the addition of acetonitrile (5 mL). The vial was sealed and heated at 120° C. in a single mode microwave for 30 minutes, and a further 60 minutes at 150° C. The product crystallised from the reaction on cooling and was subsequently filtered and washed with acetonitrile (10 mL). Purification (SiO2, 7M ammonia in methanol:methanol:dichloromethane 1:4:95) gave the title compound (0.055 g).

Workup

customThe vial was sealed
customa further 60 minutes
customat 150° C
customThe product crystallised from the reaction
temperatureon cooling
filtrationwas subsequently filtered
washwashed with acetonitrile (10 mL)
customPurification (SiO2, 7M ammonia in methanol:methanol:dichloromethane 1:4:95)

Sources & evidence

ORD record: ord-6588e761eaec4241be9beb606232846c
Source dataset: uspto-grants-2008_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07408065B2

Reaction notes

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