Chloroform → HCID 178504757, compound

HRID 869270Notes

Reaction equation

HRID 869270 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:30].ClN1C(=O)CCC1=O>C(#N)C>[Cl:30][C:14]1[N:13]=[C:12]([C:15]([NH2:17])=[O:16])[C:11]([NH:18][C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([S:25]([CH3:28])(=[O:26])=[O:27])[CH:20]=2)=[N:10][C:9]=1[NH:8][C@H:5]1[CH2:4][CH2:3][C@H:2]([OH:1])[CH2:7][CH2:6]1

Participants

5

Reactant 3

HCID 6212ChloroformHCID 31398ChlorosuccinimideHCID 178504759HCID 178504759, compound

Product 1

HCID 178504757HCID 178504757, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
70 °C

Procedure

To a mixture of 5-[(trans-4-hydroxycyclohexyl)amino]-3-{[3-(methylsulfonyl)phenyl]amino}pyrazine-2-carboxamide (Example 111) (298 mg), chloroform (40 mL) and acetonitrile (10 mL), N-chlorosuccinimide (108 mg) was added and stirred at 70° C. for 8 hours. After the reaction liquid was cooled, 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 from chloroform and collected by filtration. The resulting solid was heated with ethyl acetate and washed with ethyl acetate to give 6-chloro-5-[(trans-4-hydroxycyclohexyl)amino]-3-{[3-(methylsulfonyl)phenyl]amino}pyrazine-2-carboxamide (189 mg) as a white solid.

Workup

  1. additionwas added
  2. customAfter the reaction liquid
  3. temperaturewas cooled
  4. additionsilica gel was added
  5. distillationthe solvent was distilled off
  6. customfollowed by purification by silica gel column chromatography (eluent; chloroform:methanol=10:0 to 10:1)
  7. filtrationcollected by filtration
  8. temperatureThe resulting solid was heated with ethyl acetate
  9. washwashed with ethyl acetate

Sources & evidence

ORD record
ord-dca8313abf8641638e79dd3c522b7748
Source dataset
uspto-grants-2015_03
Patent number
US08969336B2

Reaction notes

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