Sodium Iodide → HCID 60204461, compound

HRID 2267344Notes

Reaction equation

HRID 2267344 reaction equation
CS(Cl)(=O)=O.[F:6][C:7]1[CH:40]=[CH:39][C:10]([CH2:11][C:12]2[S:16][C:15]([C:17]3[C:22]([Br:23])=[CH:21][N:20]=[C:19]([NH:24][CH2:25][CH2:26][N:27]4[C:31]([CH3:33])([CH3:32])[C:30](=[O:34])[NH:29][C:28]4=[O:35])[N:18]=3)=[CH:14][C:13]=2[CH2:36][CH2:37]O)=[CH:9][CH:8]=1.C(N(C(C)C)CC)(C)C.[I-].[Na+].[NH:52]1[CH2:56][CH2:55][CH2:54][C@H:53]1[CH2:57][OH:58]>ClCCl.O>[F:6][C:7]1[CH:40]=[CH:39][C:10]([CH2:11][C:12]2[S:16][C:15]([C:17]3[C:22]([Br:23])=[CH:21][N:20]=[C:19]([NH:24][CH2:25][CH2:26][N:27]4[C:31]([CH3:32])([CH3:33])[C:30](=[O:34])[NH:29][C:28]4=[O:35])[N:18]=3)=[CH:14][C:13]=2[CH2:36][CH2:37][N:52]2[CH2:56][CH2:55][CH2:54][C@H:53]2[CH2:57][OH:58])=[CH:9][CH:8]=1

Participants

8

Reactant 5

HCID 5238Sodium IodideHCID 31297Methanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 640091L-ProlinolHCID 11592167HCID 11592167, compound

Product 1

HCID 60204461HCID 60204461, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

Methanesulfonyl chloride (82 mg, 0.72 mmol) was added to a mixture of 1-(2-(4-(5-(4-fluorobenzyl)-4-(2-hydroxyethyl)thiophen-2-yl)-5-bromopyrimidin-2-ylamino)ethyl)-5,5-dimethylimidazolidine-2,4-dione (200 mg, 0.36 mmol) and diisopropylethylamine (93 mg, 0.72 mmol) in dichloromethane (10 mL) at 0° C. After stirring at 0° C. for 5 h, the solvent was removed in vacuo and 5 mL of N-methylpyrrolidine, a catalytic amount of sodium iodide and (S)-pyrrolidin-2-ylmethanol (0.3 g, 2.97 mmol) were added. The mixture was heated at 100° C. for 15 h and then cooled to rt. 50 mL of water was added and the mixture extracted with ethyl acetate (3×50 mL). The combined organic layers were washed with brine (3×50 mL), dried over anhydrous sodium sulfate and filtered. The solvent was removed in vacuo and the product purified by flash chromatography eluting with methanol (1M, ammonia)/dichloromethane (1:20) to give the title compound as a slightly yellow solid (105 mg, 46%). MS (M+H)+ 645/647.

Workup

  1. customthe solvent was removed in vacuo and 5 mL of N-methylpyrrolidine
  2. temperatureThe mixture was heated at 100° C. for 15 h
  3. temperaturecooled to rt
  4. extractionthe mixture extracted with ethyl acetate (3×50 mL)
  5. washThe combined organic layers were washed with brine (3×50 mL)
  6. dry with materialdried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. customThe solvent was removed in vacuo
  9. customthe product purified by flash chromatography
  10. washeluting with methanol (1M, ammonia)/dichloromethane (1:20)

Sources & evidence

ORD record
ord-967583a3ba314cf3b779039ba8d76aae
Source dataset
uspto-grants-2010_12
Patent number
US07858785B2

Reaction notes

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