Ammonia → 6-{2-[(2R)-2-methyl-pyrrolidin-1-yl]-ethyl}-2-(3-phenyl-isoxazol-5-yl)-quinoline

HRID 11336Notes

Reaction equation

HRID 11336 reaction equation
[C:1]1([C:7]2[CH:11]=[C:10]([C:12](=O)[CH3:13])[O:9][N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:15][C:16]1[N:17]=[C:18]([C:24]2S[CH:26]=[CH:27][CH:28]=2)S[C:20]=1[C:21](=O)[CH3:22].[NH3:29]>>[CH3:15][C@@H:16]1[CH2:20][CH2:21][CH2:22][N:17]1[CH2:18][CH2:24][C:28]1[CH:2]=[C:1]2[C:7](=[CH:26][CH:27]=1)[N:29]=[C:12]([C:10]1[O:9][N:8]=[C:7]([C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)[CH:11]=1)[CH:13]=[CH:6]2

Participants

4

Reactant 3

HCID 222AmmoniaHCID 27352641-(3-Phenyl-1,2-oxazol-5-yl)ethan-1-oneHCID 27442451-[4-Methyl-2-(2-thienyl)-1,3-thiazol-5-yl]-1-ethanone

Product 1

HCID 115817616-{2-[(2R)-2-methyl-pyrrolidin-1-yl]-ethyl}-2-(3-phenyl-isoxazol-5-yl)-quinoline

Procedure

The title compound was prepared using the procedure described in Example 1G substituting 1-(3-phenyl-isoxazol-5-yl)-ethanone (Ohsawa, A. et. al. Heterocycles 1978, 9, pages 1367–1373) for 1-(4-methyl-2-thiophen-2-yl-thiazol-5-yl)-ethanone. 1H NMR (300 MHz, CD3OD) δ 1.18 (d, J=6 Hz, 3H), 1.50 (m, 1H), 1.82 (m, 2H), 2.04 (m, 1H), 2.39 (q, J=6 Hz, 1H), 2.52 (m, 2H), 3.08 (m, 2H), 3.22 (m, 2H), 7.53 (m, 3H), 7.64 (s, 1H), 7.78 (dd, J=9 Hz, J=3 Hz, 1H), 7.85 (s, 1H), 7.99 (m, 2H), 8.10 (dd, J=9 Hz, J=3 Hz, 2H), 8.45 (d, J=9 Hz, 1H); MS (DCI/NH3) m/z 384 (M+H)+.

Sources & evidence

ORD record
ord-45d9adc2864247e5b37288957c003c94
Source dataset
uspto-grants-2006_08
Patent number
US07098222B2

Reaction notes

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