Chlorosuccinimide → HCID 57693557, compound

HRID 1516862Notes

Reaction equation

HRID 1516862 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-c46d4af661f84c249e7ea8a58423015c
Source dataset
uspto-grants-2012_07
Patent number
US08227601B2

Reaction notes

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