Chloroform → HCID 178504755, compound

HRID 869271Notes

Reaction equation

HRID 869271 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.[Br:33]N1C(=O)CCC1=O>C(#N)C>[Br:33][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 67184N-bromobutanimideHCID 178504759HCID 178504759, compound

Product 1

HCID 178504755HCID 178504755, compoundYield 72.5%

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-bromosuccinimide (69 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=10:0:0 to 10:1). The resulting crude product was solidified with ethyl acetate and washed with ethyl acetate to give 6-bromo-5-[(trans-4-hydroxycyclohexyl)amino]-3-{[3-(methylsulfonyl)phenyl]amino}pyrazine-2-carboxamide (130 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=10:0:0 to 10:1)
  6. washwashed with ethyl acetate

Sources & evidence

ORD record
ord-3f1d4b1a30e5407587f7afc78105ef3d
Source dataset
uspto-grants-2015_03
Patent number
US08969336B2

Reaction notes

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