Chlorosuccinimide → HCID 57693624, compound

HRID 1516867Notes

Reaction equation

HRID 1516867 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-f427a10d8c0c46708d080f981afd222b
Source dataset
uspto-grants-2012_07
Patent number
US08227601B2

Reaction notes

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