Sodium Iodide → HCID 10074641, compound

HRID 2087237Notes

Reaction equation

Cl[CH2:2][CH2:3][C@@H:4]([O:11][C:12]1[CH:13]=[C:14]([C:18](=[O:20])[CH3:19])[CH:15]=[CH:16][CH:17]=1)[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.[CH3:21][CH:22]([CH3:38])[C:23]([NH:25][C:26]1[CH:31]=[CH:30][CH:29]=[C:28]([CH:32]2[CH2:37][CH2:36][NH:35][CH2:34][CH2:33]2)[CH:27]=1)=[O:24].[Na+].[I-].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[C:18]([C:14]1[CH:13]=[C:12]([CH:17]=[CH:16][CH:15]=1)[O:11][C@@H:4]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)[CH2:3][CH2:2][N:35]1[CH2:36][CH2:37][CH:32]([C:28]2[CH:27]=[C:26]([NH:25][C:23](=[O:24])[CH:22]([CH3:21])[CH3:38])[CH:31]=[CH:30][CH:29]=2)[CH2:33][CH2:34]1)(=[O:20])[CH3:19]

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of 1-(3-{[(1R)-3-chloro-1-phenylpropyl]oxy}phenyl)ethanone (58.5 mg, 0.200 mmol), 2-methyl-N-[3-(4-piperidinyl)phenyl]propanamide (56.8 mg, 0.200 mmol), NaI (34.0 mg, 0.200 mmol) and K2CO3 (55.5 mg, 0.400 mmol) in DMF (1.00 mL) was stirred at 100° C. for 3 h. The solvent was removed under reduced pressure and the residue was purified by chromatography on silica using 5% of NH3 (2.0 M in methanol) in CH2Cl2 to give the desired product (98.0 mg, 98.0%): 1H NMR (400 MHz, CDCl3) δ 8.01 (s, 1H), 7.49-7.21 (m, 11H), 7.09-7.03 (m, 1H), 6.96 (d, 1H, J=7.9 Hz), 5.32 (dd, 1H, J=5.0, 7.9 Hz), 3.08-2.98 (m, 2H), 2.57-2.43 (m, 6H), 2.11-1.72 (m, 9H), 1.25 (d, 6H, J=6.8 Hz); ESMS m/e: 499.4 (M+H)+.

Workup

customThe solvent was removed under reduced pressure
customthe residue was purified by chromatography on silica using 5% of NH3 (2.0 M in methanol) in CH2Cl2

Sources & evidence

ORD record: ord-fdc413260efc4a7caa133bbe876a8111
Source dataset: uspto-grants-2004_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06727264B1

Reaction notes

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