8-Mercaptoquinoline → HCID 9802462, compound

HRID 987587Notes

Reaction equation

HRID 987587 reaction equation
Cl[CH2:2][CH2:3][N:4]1[CH:9]2[CH2:10][CH2:11][CH:5]1[CH2:6][CH:7]([C:12]1[CH:21]=[CH:20][C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[CH:13]=1)[CH2:8]2.[N:22]1[C:31]2[C:26](=[CH:27][CH:28]=[CH:29][C:30]=2[SH:32])[CH:25]=[CH:24][CH:23]=1>>[CH:13]1[C:14]2[C:19](=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:20]=[CH:21][C:12]=1[CH:7]1[CH2:6][CH:5]2[N:4]([CH2:3][CH2:2][S:32][C:30]3[CH:29]=[CH:28][CH:27]=[C:26]4[C:31]=3[N:22]=[CH:23][CH:24]=[CH:25]4)[CH:9]([CH2:10][CH2:11]2)[CH2:8]1

Participants

3

Reactant 2

HCID 960288-MercaptoquinolineHCID 11472093HCID 11472093, compound

Product 1

HCID 9802462HCID 9802462, compound

Procedure

The title compound was prepared by the procedure described in Example 8, Step 5, except that 8-(2-chloroethyl)-3-(2-naphthyl)-8-azabicyclo[3.2.1]octane was used in place of 8-(2-chloroethyl)-3-(2-naphthyl)-8-azabicyclo[3.2.1]oct-2-ene, and 8-quinolinethiol was used in place of 6-methoxyquinolin-8-ol. Yield: 36% of a tan solid. The corresponding oxalate salt was prepared by combining the title compound with 1 equiv. of oxalic acid in CH2Cl2/MeOH to precipitate a white solid. Yield: 71%; mp: 200-203° C.; MS (ES) m/z: 425.

Sources & evidence

ORD record
ord-198ed85c69994439979e9a5b1d1e8a3d
Source dataset
uspto-grants-2003_10
Patent number
US06632824B2

Reaction notes

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