Ammonia → 2-[3-(3-Chloro-5-trifluoromethyl-pyridin-2-yl)-isoxazol-5-yl]-6-[2-((2R)-2-methyl-pyrrolidin-1-yl)-ethyl]-quinoline

HRID 11330Notes

Reaction equation

HRID 11330 reaction equation
[Cl:1][C:2]1[C:3]([C:12]2[CH:16]=[C:15]([C:17](=O)[CH3:18])[O:14][N:13]=2)=[N:4][CH:5]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:7]=1.[CH3:20][C:21]1[N:22]=[C:23]([C:29]2S[CH:31]=[CH:32][CH:33]=2)S[C:25]=1[C:26](=O)[CH3:27].[NH3:34]>>[Cl:1][C:2]1[C:3]([C:12]2[CH:16]=[C:15]([C:17]3[CH:18]=[CH:8][C:6]4[C:5](=[CH:31][CH:32]=[C:33]([CH2:29][CH2:23][N:22]5[CH2:27][CH2:26][CH2:25][C@H:21]5[CH3:20])[CH:7]=4)[N:34]=3)[O:14][N:13]=2)=[N:4][CH:5]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:7]=1

Participants

4

Reactant 3

HCID 222AmmoniaHCID 27442451-[4-Methyl-2-(2-thienyl)-1,3-thiazol-5-yl]-1-ethanoneHCID 36039151-{3-[3-Chloro-5-(trifluoromethyl)-2-pyridinyl]-5-isoxazolyl}-1-ethanone

Product 1

HCID 117200662-[3-(3-Chloro-5-trifluoromethyl-pyridin-2-yl)-isoxazol-5-yl]-6-[2-((2R)-2-methyl-pyrrolidin-1-yl)-ethyl]-quinoline

Procedure

The title compound was prepared using the procedure described in Example 1G using 1-[3-(3-chloro-5-trifluoromethyl-pyridin-2-yl)-isoxazol-5-yl]-ethanone (Key Organics Limited/Bionet Research, catalog number 10G-001) for 1-(4-methyl-2-thiophen-2-yl-thiazol-5-yl)-ethanone. 1H NMR (300 MHz, CDCl3) δ 1.13 (d, J=6.10 Hz, 3H), 1.46 (m, 1H), 1.79 (m, 2H), 1.95 (m, 1H), 2.25 (q, J=8.59 Hz, 1H), 2.40 (m, 2H), 3.04 (m, 2H), 3.15 (m, 1H), 3.29 (td, J=8.56, 2.88 Hz, 1H), 7.69 (m, 3H), 8.10 (m, 3H), 8.27 (d, J=8.48 Hz, 1H), 8.93 (d, J=2.03 Hz, 1H); MS (DCI-NH3) [M+H]+ at 487.

Sources & evidence

ORD record
ord-330d9917cf7b4c2a9e7c6f80741572bb
Source dataset
uspto-grants-2006_08
Patent number
US07098222B2

Reaction notes

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