Chlorosuccinimide → HCID 57693624, compound

HRID 1805886Notes

Reaction equation

HRID 1805886 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([NH:9][C:10]2[N:11]=[C:12]([O:19][C:20]3[C:27]([CH3:28])=[CH:26][C:23]([C:24]#[N:25])=[CH:22][C:21]=3[CH3:29])[C:13]3[NH:18][CH:17]=[CH:16][C:14]=3[N:15]=2)=[CH:5][CH:4]=1)#[N:2].C1C(=O)N([Cl:37])C(=O)C1>C(Cl)Cl>[Cl:37][C:16]1[C:14]2[N:15]=[C:10]([NH:9][C:6]3[CH:7]=[CH:8][C:3]([C:1]#[N:2])=[CH:4][CH:5]=3)[N:11]=[C:12]([O:19][C:20]3[C:21]([CH3:29])=[CH:22][C:23]([C:24]#[N:25])=[CH:26][C:27]=3[CH3:28])[C:13]=2[NH:18][CH:17]=1

Participants

4

Reactant 2

HCID 31398ChlorosuccinimideHCID 11954403HCID 11954403, compound

Product 1

HCID 57693624HCID 57693624, compoundYield 68.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-(2-(4-cyanophenylamino)-5H-pyrrolo[3,2-d]pyrimidin-4-yloxy)-3,5-dimethylbenzonitrile (28.1 mg, 0.07 mmol) in CH2Cl2 (4 mL) was added NCS (9.9 mg, 0.07 mmol) and the resultant mixture was refluxed for 16 h. After completion of the reaction, the solvent was concentrated and purified by preparative TLC eluting with hexanes:ethyl acetate (2:1), to give the product as a pink solid (20 mg, 65%).

Workup

  1. customAfter completion of the reaction
  2. concentrationthe solvent was concentrated
  3. custompurified by preparative TLC
  4. washeluting with hexanes:ethyl acetate (2:1)

Sources & evidence

ORD record
ord-88508ce80e70457098b3f4bca7d7e559
Source dataset
uspto-grants-2013_01
Patent number
US08354532B2

Reaction notes

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