2-Aminobenzonitrile → HCID 178482916, compound

HRID 392627Notes

Reaction equation

HRID 392627 reaction equation
[Li+].C[Si]([N-][Si](C)(C)C)(C)C.[CH3:11][N:12]([CH3:33])[CH:13]1[CH2:17][CH2:16][N:15]([C:18]2[N:23]=[C:22]3[NH:24][C:25]([CH2:27][C:28]([O:30]CC)=O)=[N:26][C:21]3=[CH:20][CH:19]=2)[CH2:14]1.[NH2:34][C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][C:36]=1[C:41]#[N:42]>C1COCC1>[NH2:42][C:41]1[C:36]2[C:35](=[CH:40][CH:39]=[CH:38][CH:37]=2)[NH:34][C:28](=[O:30])[C:27]=1[C:25]1[NH:24][C:22]2=[N:23][C:18]([N:15]3[CH2:16][CH2:17][CH:13]([N:12]([CH3:11])[CH3:33])[CH2:14]3)=[CH:19][CH:20]=[C:21]2[N:26]=1

Participants

5

Reactant 3

HCID 729132-AminobenzonitrileHCID 2733832Lithium HexamethyldisilazideHCID 178470770HCID 178470770, compound

Product 1

HCID 178482916HCID 178482916, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

LiHMDS (3.5 eq) was added to ethyl {5-[3-(dimethylamino)pyrrolidin-1-yl]-3H-imidazo[4,5-b]pyridin-2-yl}acetate (1.0 eq) in THF at −40° C. After 10 minutes, a solution of 2-aminobenzenecarbonitrile (1.1 eq) in THF was added. The resulting mixture was allowed to warm to room temperature, stirred for 1 h and then heated to 60° C. overnight. The mixture was cooled to room temperature and quenched with NH4Cl (aq, saturated). The aqueous phase was extracted with CH2Cl2 (5 times). The product crashes out of the organic solution during the extractions. Evaporation of the solvent under reduced pressure afforded a brown solid that was triturated repeatedly with MeOH and acetone to obtain a yellow greenish powder. LC/MS m/z 390.2 (MH+), Rt 1.48 minutes.

Workup

  1. temperatureheated to 60° C. overnight
  2. temperatureThe mixture was cooled to room temperature
  3. customquenched with NH4Cl (aq, saturated)
  4. extractionThe aqueous phase was extracted with CH2Cl2 (5 times)
  5. extractionThe product crashes out of the organic solution during the extractions
  6. customEvaporation of the solvent under reduced pressure
  7. customafforded a brown solid that
  8. customwas triturated repeatedly with MeOH and acetone
  9. customto obtain a yellow greenish powder

Sources & evidence

ORD record
ord-d72f4a8858d04e8eb59e3c4bdd013c51
Source dataset
uspto-grants-2004_10
Patent number
US06800760B2

Reaction notes

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