Potassium Iodide → HCID 11577086, compound

HRID 1685541Notes

Reaction equation

HRID 1685541 reaction equation
[CH:1]1([CH2:6][C@H:7]([C:19]2[CH:24]=[CH:23][C:22]([S:25]([CH3:28])(=[O:27])=[O:26])=[CH:21][CH:20]=2)[C:8]([NH:10][C:11]2[S:12][C:13]([S:16]C#N)=[CH:14][N:15]=2)=[O:9])[CH2:5][CH2:4][CH2:3][CH2:2]1.SC[C@H]([C@@H](CS)O)O.Cl[CH2:38][CH2:39][N:40]([CH2:43][CH3:44])[CH2:41][CH3:42].C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>CO.C(Cl)Cl.O>[CH:1]1([CH2:6][C@H:7]([C:19]2[CH:20]=[CH:21][C:22]([S:25]([CH3:28])(=[O:26])=[O:27])=[CH:23][CH:24]=2)[C:8]([NH:10][C:11]2[S:12][C:13]([S:16][CH2:38][CH2:39][N:40]([CH2:43][CH3:44])[CH2:41][CH3:42])=[CH:14][N:15]=2)=[O:9])[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

9

Reactant 5

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 13364Diethylaminoethyl chlorideHCID 446094D-1,4-DithiothreitolHCID 11690640HCID 11690640, compound

Product 1

HCID 11577086HCID 11577086, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of (R)-3-cyclopentyl-2-(4-methanesulfonyl-phenyl)-N-(5-thiocyanato-thiazol-2-yl)-propionamide (200 mg, 0.46 mmol) in methanol (2.5 mL) and DCM (2.5 mL) was added dithiothreitol (71 mg, 0.46 mmol), and the mixture was stirred at room temperature for 1 h. 2-Chloroethyl-diethylamine (158 mg, 0.92 mmol), potassium carbonate (235 mg, 0.46 mmol), and potassium iodide (10 mg) were added and the reaction mixture was stirred for another 3 h at room temperature. Water (5 mL) and DCM (10 mL) were added and the organic phase was isolated and dried over anhydrous magnesium sulphate. The solvent was removed in vacuo, and the residue was purified on a silica gel column (isocratic from 100% DMC to 100% ethyl acetate with 1% TEA) to give colourless crystals of (R)-3-cyclopentyl-N-[5-(2-diethylamino-ethylsulfanyl)-thiazol-2-yl]-2-(4-methanesulfonyl-phenyl)-propionamide. Yield: 150 mg (64%). 1H-NMR (CDCl3): δ 11.50 (broad s, 1H), 7.86 (d, 2H), 7.51 (d, 2H), 7.48 (s, 1H), 3.76 (t, 1H), 3.04 (s, 3H), 2.86 (t, 2H), 2.71 (t, 2H), 2.54 (q, 4H), 2.26 (m, 1H), 1.90 (m, 1H), 1.79-1.43 (m, 8H), 1.12 (m, 1H), 1.00 (t, 6H); HPLC-MS: m/z=510 (M+1).

Workup

  1. stirringthe reaction mixture was stirred for another 3 h at room temperature
  2. customthe organic phase was isolated
  3. dry with materialdried over anhydrous magnesium sulphate
  4. customThe solvent was removed in vacuo
  5. customthe residue was purified on a silica gel column (isocratic from 100% DMC to 100% ethyl acetate with 1% TEA)

Sources & evidence

ORD record
ord-07ed5a5cd39d4c56869b3181d68c0e69
Source dataset
uspto-grants-2012_04
Patent number
US08148412B2

Reaction notes

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