Sodium Iodide → HCID 46240338, compound

HRID 1710800Notes

Reaction equation

Cl[CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2[S:13][C:14]([C:18]([N:20]3[CH2:25][CH2:24][O:23][CH2:22][CH2:21]3)=[O:19])=[C:15]([CH3:17])[N:16]=2)=[CH:8][CH:7]=1.C(=O)([O-])[O-].[K+].[K+].[I-].[Na+].[CH3:34][CH:35]1[CH2:39][CH2:38][CH2:37][NH:36]1>C(#N)C.C(OCC)(=O)C>[CH3:17][C:15]1[N:16]=[C:12]([C:9]2[CH:10]=[CH:11][C:6]([O:5][CH2:4][CH2:3][CH2:2][N:36]3[CH2:37][CH2:38][CH2:39][CH:35]3[CH3:34])=[CH:7][CH:8]=2)[S:13][C:14]=1[C:18]([N:20]1[CH2:25][CH2:24][O:23][CH2:22][CH2:21]1)=[O:19]

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of 4-({2-[4-(3-chloropropoxy)phenyl]-4-methyl-1,3-thiazol-5-yl}carbonyl)morpholine i107 (1.0 mmol, 1 eq, 0.38 g) in acetonitrile (10 ml), is added potassium carbonate (1.99 mmol, 2 eq, 0.27 g) and approximately 0.01 g of sodium iodide. The mixture is stirred at 80° C. for 30 minutes in a sealed tube before addition of 2-methylpyrrolidine (1.2 mmol, 1.2 eq, 0.12 ml). The mixture is then stirred at 80° C. overnight. The mixture is taken up in ethyl acetate and washed with a saturated solution of sodium bicarbonate, then dried over magnesium sulfate. The solvent is removed under reduced pressure and purified by chromatography over silica gel (eluent: dichloromethane/methanol/ammonia 96:3.6:0.4) to give 0.132 g of 4-[(4-methyl-2-{4-[3-(2-methylpyrrolidin-1-yl)propoxy]phenyl}-1,3-thiazol-5-yl)carbonyl]morpholine 152 as a yellow oil.

Workup

washwashed with a saturated solution of sodium bicarbonate
dry with materialdried over magnesium sulfate
customThe solvent is removed under reduced pressure
custompurified by chromatography over silica gel (eluent: dichloromethane/methanol/ammonia 96:3.6:0.4)

Sources & evidence

ORD record: ord-5445e62c8324456b9004b7063d85d7c6
Source dataset: uspto-grants-2010_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07790720B2

Reaction notes

Loading…