Thiophenol → HCID 66875074, compound
Reaction equation
I[C:2]1[CH:7]=[N:6][N:5](C2CCCCO2)[C:4](=[O:14])[CH:3]=1.[C:15]1([SH:21])[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>>[C:15]1([S:21][C:2]2[CH:7]=[N:6][NH:5][C:4](=[O:14])[CH:3]=2)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1Participants
Procedure
In an analogous manner to the stepwise sequence outlined in Intermediate 18, starting from 5-iodo-2-(tetrahydro-pyran-2-yl)-2H-pyridazin-3-one (Intermediate 18, step 2) and benzenethiol afforded 5-phenylsulfanyl-2H-pyridazin-3-one which was then reacted in an analogous manner to that outlined in the synthesis of intermediate 19 (steps 4 and 5) alkylating with 2-bromo-3-cyclopentyl-propionic acid methyl ester (Intermediate 10) afforded the lithium salt of 3-cyclopentyl-2-(6-oxo-4-phenylsulfanyl-6H-pyridazin-1-yl)-propionic acid as a white solid (98 mg, quantitative for the final step); ES+-HRMS m/e calcd for C18H20N2O3SI [M+H+] 345.1268, found 345.1268. 1H NMR (300 MHz, DMSO-d6) δ ppm 0.93-1.19 (m, 2H), 1.29-1.76 (m, 7H), 1.86-2.00 (m, 1H), 2.05-2.21 (m, 1H), 5.24 (dd, J=10.9, 3.9 Hz, 1H), 5.94 (d, J=2.1 Hz, 1H), 7.53-7.64 (m, 3H), 7.63-7.73 (m, 2H), 7.91 (d, J=2.1 Hz, 1H), 13.02 (br. s., 1H).
Sources & evidence
- ORD record
- ord-28e2eaa6c9a34d13a9d7b37d9328b7d1
- Source dataset
- uspto-grants-2012_09
- Patent number
- US08258134B2
Reaction notes
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