Chlorosuccinimide → HCID 57693557, compound

HRID 1805882Notes

Reaction equation

HRID 1805882 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([Cl:36])C(=O)C1>C(Cl)Cl>[Cl: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 31398ChlorosuccinimideHCID 57693558HCID 57693558, compound

Product 1

HCID 57693557HCID 57693557, compoundYield 104.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-(4-(mesitylthio)-5H-pyrrolo[3,2-d]pyrimidin-2-ylamino)benzonitrile (10 mg, 0.02 mmol) in CH2Cl2 (5 mL) was added NCS (2.8 mg, 0.02 mmol) and the resolution mixture refluxed for 16 h. After the completion of the reaction, the solvent was concentrated and purified by preparative TLC, eluting with hexanes:ethyl acetate (3:1), to give the product (8.8 mg, 88%).

Workup

  1. temperaturethe resolution mixture refluxed for 16 h
  2. customAfter the completion of the reaction
  3. concentrationthe solvent was concentrated
  4. custompurified by preparative TLC
  5. washeluting with hexanes:ethyl acetate (3:1)

Sources & evidence

ORD record
ord-57cfc12d71b0465a89b646c261e9a564
Source dataset
uspto-grants-2013_01
Patent number
US08354532B2

Reaction notes

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