Chloroform → HCID 178504758, compound

HRID 869272Notes

Reaction equation

HRID 869272 reaction equation
[OH:1][C@H:2]1[CH2:7][CH2:6][C@H:5]([NH:8][C:9]2[N:10]=[C:11]([NH:18][C:19]3[CH:24]=[CH:23][CH:22]=[C:21]([S:25]([CH3:28])(=[O:27])=[O:26])[CH:20]=3)[C:12]([C:15]([NH2:17])=[O:16])=[N:13][CH:14]=2)[CH2:4][CH2:3]1.C(Cl)(Cl)Cl.[I:33]N1C(=O)CCC1=O>C(#N)C>[OH:1][C@H:2]1[CH2:3][CH2:4][C@H:5]([NH:8][C:9]2[N:10]=[C:11]([NH:18][C:19]3[CH:24]=[CH:23][CH:22]=[C:21]([S:25]([CH3:28])(=[O:26])=[O:27])[CH:20]=3)[C:12]([C:15]([NH2:17])=[O:16])=[N:13][C:14]=2[I:33])[CH2:6][CH2:7]1

Participants

5

Reactant 3

HCID 6212ChloroformHCID 120273N-IodosuccinimideHCID 178504759HCID 178504759, compound

Product 1

HCID 178504758HCID 178504758, compoundYield 77.8%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a mixture of 5-[(trans-4-hydroxycyclohexyl)amino]-3-{[3-(methylsulfonyl)phenyl]amino}pyrazine-2-carboxamide (Example 111) (150 mg), chloroform (40 mL) and acetonitrile (20 mL), N-iodosuccinimide (87 mg) was added and stirred at room temperature for 2 hours. To the reaction liquid, silica gel was added, and the solvent was distilled off, followed by purification by silica gel column chromatography (eluent; chloroform:methanol=10:0 to 10:1). The resulting crude product was solidified with ethyl acetate and washed with ethyl acetate to give 5-[(trans-4-hydroxycyclohexyl)amino]-6-iodo-3-{[3-(methylsulfonyl)phenyl]amino}pyrazine-2-carboxamide (153 mg) as a light yellow solid.

Workup

  1. additionwas added
  2. customTo the reaction liquid, silica gel
  3. additionwas added
  4. distillationthe solvent was distilled off
  5. customfollowed by purification by silica gel column chromatography (eluent; chloroform:methanol=10:0 to 10:1)
  6. washwashed with ethyl acetate

Sources & evidence

ORD record
ord-a59f64c8ea9446019e0847409a7eed95
Source dataset
uspto-grants-2015_03
Patent number
US08969336B2

Reaction notes

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