Ammonia → 6-[2-((2R)-2-Methyl-pyrrolidin-1-yl)-ethyl]-2-(1-pyridin-3-yl-cyclobutyl)-quinoline

HRID 11335Notes

Reaction equation

HRID 11335 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7]2([C:11](=O)[CH3:12])[CH2:10][CH2:9][CH2:8]2)[CH:2]=1.[CH3:14][C:15]1[N:16]=[C:17]([C:23]2S[CH:25]=[CH:26][CH:27]=2)S[C:19]=1[C:20](=O)[CH3:21].[NH3:28]>>[CH3:14][C@@H:15]1[CH2:19][CH2:20][CH2:21][N:16]1[CH2:17][CH2:23][C:27]1[CH:2]=[C:3]2[C:7](=[CH:25][CH:26]=1)[N:28]=[C:11]([C:7]1([C:3]3[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=3)[CH2:10][CH2:9][CH2:8]1)[CH:12]=[CH:4]2

Participants

4

Reactant 3

HCID 222AmmoniaHCID 27442451-[4-Methyl-2-(2-thienyl)-1,3-thiazol-5-yl]-1-ethanoneHCID 219738511-(1-Pyridin-3-yl-cyclobutyl)-ethanone

Product 1

HCID 115597596-[2-((2R)-2-Methyl-pyrrolidin-1-yl)-ethyl]-2-(1-pyridin-3-yl-cyclobutyl)-quinoline

Procedure

The title compound was prepared using the procedure described in Example 1G using 1-(1-pyridin-3-yl-cyclobutyl)-ethanone for 1-(4-methyl-2-thiophen-2-yl-thiazol-5-yl)-ethanone. 1H NMR (300 MHz, CDCl3) δ 1.12 (d, J=6.10 Hz, 3H), 1.46 (m, 1H), 1.75 (m, 2H), 1.92 (m, 1H), 2.05 (m, 2H), 2.23 (q, J=8.82 Hz, 1H), 2.37 (m, 2H), 2.77 (m, 2H), 2.94-3.22 (m, 5H), 3.28 (m, 1H), 7.17 (m, 1H), 7.19 (m, 1H), 7.56 (s, 1H), 7.58 (dd, J=8.48, 2.03 Hz, 1H), 7.65 (ddd, J=8.05, 2.46, 1.70 Hz, 1H), 7.95 (d, J=8.81 Hz, 1H), 8.04 (d, J=8.48 Hz, 1H), 8.41 (dd, J=4.75, 1.70 Hz, 1H), 8.70 (dd, J=2.37, 0.68 Hz, 1H); MS (DCI-NH3) [M+H]+ at 372.

Sources & evidence

ORD record
ord-321dd009aec047248955cac5da64cb75
Source dataset
uspto-grants-2006_08
Patent number
US07098222B2

Reaction notes

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