Ammonia → (R)-3-(4-chlorophenyl)-5-methyl-4-(6-(2-(2-methylpyrrolidin-1-yl)ethyl)quinolin-2-yl)isoxazole

HRID 11331Notes

Reaction equation

HRID 11331 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:12]([C:13](=O)[CH3:14])=[C:11]([CH3:16])[O:10][N:9]=2)=[CH:4][CH:3]=1.[CH3:17][C:18]1[N:19]=[C:20]([C:26]2S[CH:28]=[CH:29][CH:30]=2)S[C:22]=1[C:23](=O)[CH3:24].[NH3:31]>>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:12]([C:13]3[CH:14]=[CH:8][C:5]4[C:4](=[CH:28][CH:29]=[C:30]([CH2:26][CH2:20][N:19]5[CH2:24][CH2:23][CH2:22][C@H:18]5[CH3:17])[CH:6]=4)[N:31]=3)=[C:11]([CH3:16])[O:10][N:9]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 222AmmoniaHCID 27352401-[3-(4-Chlorophenyl)-5-Methylisoxazol-4-Yl]Ethan-1-OneHCID 27442451-[4-Methyl-2-(2-thienyl)-1,3-thiazol-5-yl]-1-ethanone

Product 1

HCID 11640588(R)-3-(4-chlorophenyl)-5-methyl-4-(6-(2-(2-methylpyrrolidin-1-yl)ethyl)quinolin-2-yl)isoxazole

Procedure

The title compound was prepared using the procedure described in Example 1G-substituting 1-[3-(4-chloro-phenyl)-5-methyl-isoxazol-4-yl]-ethanone (CAS # 169814-48-6, Maybridge Chemical Company Ltd., catalog number SPB 04957) for 1-(4-methyl-2-thiophen-2-yl-thiazol-5-yl)-ethanone. 1H NMR (300 MHz, CDCl3) δ 1.14 (d, J=5.76 Hz, 3H), 1.47 (m, 1H), 1.78 (m, 2H), 1.96 (m, 1H), 2.25 (q, J=8.70 Hz, 1H), 2.40 (m, 2H), 2.68 (s, 3H), 3.03 (m, 2H), 3.15 (m, 1H), 3.30 (td, J=8.39, 2.54 Hz, 1H), 7.08 (d, J=8.48 Hz, 1H), 7.32 (ddd, J=8.65, 2.20, 2.03 Hz, 2H), 7.45 (ddd, J=8.65, 2.37, 2.20 Hz, 2H), 7.65 (m, 2H), 8.01 (d, J=8.48 Hz, 1H), 8.03 (d, J=8.82 Hz, 1H); MS (DCI-NH3) [M+H]+ at 432.

Sources & evidence

ORD record
ord-2937c7d99e2f4511bfd8c1d0c0900d6b
Source dataset
uspto-grants-2006_08
Patent number
US07098222B2

Reaction notes

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