HCID 86684149, compound → 6-Chloro-N-(5-(4-(oxetan-3-yl)piperazin-1-yl)pyridin-2-yl)-1H-benzo[d]imidazol-4-amine

HRID 1024072Notes

Reaction equation

HRID 1024072 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH:19][C:20]2[CH:25]=[CH:24][C:23]([N:26]3[CH2:31][CH2:30][N:29]([CH:32]4[CH2:35][O:34][CH2:33]4)[CH2:28][CH2:27]3)=[CH:22][N:21]=2)[C:5]2[N:9]=[CH:8][N:7](COCC[Si](C)(C)C)[C:6]=2[CH:18]=1>C(O)(C(F)(F)F)=O>[Cl:1][C:2]1[CH:3]=[C:4]([NH:19][C:20]2[CH:25]=[CH:24][C:23]([N:26]3[CH2:31][CH2:30][N:29]([CH:32]4[CH2:35][O:34][CH2:33]4)[CH2:28][CH2:27]3)=[CH:22][N:21]=2)[C:5]2[N:9]=[CH:8][NH:7][C:6]=2[CH:18]=1

Participants

3

Reactant 1

HCID 86684149HCID 86684149, compound

Product 1

HCID 866841506-Chloro-N-(5-(4-(oxetan-3-yl)piperazin-1-yl)pyridin-2-yl)-1H-benzo[d]imidazol-4-amineYield 93%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A mixture of 116b (720 mg, 1.4 mmol) in TFA (10 mL) was stirred at room temperature for 6 h. The mixture was concentrated under reduced pressure and the diluted with water (10 mL). The pH of the mixture was adjusted to 7 by adding aqueous ammonia. It was then extracted with dichloromethane (3×20 mL). The combined organic phase was dried over anhydrous Na2SO4, filtered, and evaporated under reduced pressure to afford 116c as a brown solid (500 mg, 93%). MS-ESI: [M+H]+ 385.1

Workup

  1. concentrationThe mixture was concentrated under reduced pressure
  2. additionthe diluted with water (10 mL)
  3. additionby adding aqueous ammonia
  4. extractionIt was then extracted with dichloromethane (3×20 mL)
  5. dry with materialThe combined organic phase was dried over anhydrous Na2SO4
  6. filtrationfiltered
  7. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-29b3e60f0d2a48808ab7e15f48c39b16
Source dataset
uspto-grants-2014_05
Patent number
US08722676B2

Reaction notes

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