N-bromobutanimide → HCID 57693612, compound

HRID 1516863Notes

Reaction equation

HRID 1516863 reaction equation
[C:1]1([CH3:28])[CH:6]=[C:5]([CH3:7])[CH:4]=[C:3]([CH3:8])[C:2]=1[S:9][C:10]1[C:11]2[NH:27][CH:26]=[CH:25][C:12]=2[N:13]=[C:14]([NH:16][C:17]2[CH:24]=[CH:23][C:20]([C:21]#[N:22])=[CH:19][CH:18]=2)[N:15]=1.C1C(=O)N([Br:36])C(=O)C1>C(Cl)Cl>[Br:36][C:25]1[C:12]2[N:13]=[C:14]([NH:16][C:17]3[CH:24]=[CH:23][C:20]([C:21]#[N:22])=[CH:19][CH:18]=3)[N:15]=[C:10]([S:9][C:2]3[C:3]([CH3:8])=[CH:4][C:5]([CH3:7])=[CH:6][C:1]=3[CH3:28])[C:11]=2[NH:27][CH:26]=1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 57693558HCID 57693558, compound

Product 1

HCID 57693612HCID 57693612, compoundYield 23%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-(4-(mesitylthio)-5H-pyrrolo[3,2-d]pyrimidin-2-ylamino)benzonitrile (22.7 mg, 0.06 mmol) in CH2Cl2 (10 mL) was added NBS (10.5 mg, 0.06 mmol) and the resultant mixture was refluxed for 16 h. After completion of the reaction, the solvent was concentrated and purified by reversed phase HPLC to give the product as a white solid (6.4 mg, 23%).

Workup

  1. customAfter completion of the reaction
  2. concentrationthe solvent was concentrated
  3. custompurified by reversed phase HPLC

Sources & evidence

ORD record
ord-483fb357e63346278e7cf846e891870e
Source dataset
uspto-grants-2012_07
Patent number
US08227601B2

Reaction notes

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