Triethylamine → N-[6-Chloro-2-[(3R)-3-hydroxy-1-piperidinyl]-5-quinolinyl]-cyclohexaneacetamide

HRID 2217834Notes

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.Cl.[NH:24]1[CH2:29][CH2:28][CH2:27][C@@H:26]([OH:30])[CH2:25]1.C(N(CC)CC)C>C(#N)C>[Cl:22][C:7]1[C:8]([NH:12][C:13](=[O:21])[CH2:14][CH:15]2[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]2)=[C:9]2[C:4](=[CH:5][CH:6]=1)[N:3]=[C:2]([N:24]1[CH2:29][CH2:28][CH2:27][C@@H:26]([OH:30])[CH2:25]1)[CH:11]=[CH:10]2

Participants

Conditions

Temperature: 120 °C

Procedure

N-(2,6-Dichloro-5-quinolinyl)-cyclohexaneacetamide (Example 1(a)) (1 g), (3R)-3-piperidinol hydrochloride (0.424 g) and triethylamine (1.2 mL) were placed into a 10 mL microwave vial followed by the addition of acetonitrile (3 mL). The vial was sealed and heated at 120° C. in a single mode microwave for 45 minutes. On cooling a solid crystallised from the reaction mixture which was filtered and washed with acetonitrile (10 mL) to afford the sub-title compound (0.7 g).

Workup

customThe vial was sealed
temperatureOn cooling a solid
customcrystallised from the reaction mixture which
filtrationwas filtered
washwashed with acetonitrile (10 mL)

Sources & evidence

ORD record: ord-e82e0924a146438aafd31e1ac71b3359
Source dataset: uspto-grants-2008_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07408065B2

Reaction notes

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