Ammonia → 5-Ethyl-9H-dipyrido[2,3-b;4',3'-d]pyrrole-6-carbonitrile

HRID 1505969Notes

Reaction equation

HRID 1505969 reaction equation
C1(S([N:10]2[C:14]3[CH:15]=[N:16][C:17]([C:21]#[N:22])=[C:18]([CH2:19][CH3:20])[C:13]=3[C:12]3[CH:23]=[CH:24][CH:25]=[N:26][C:11]2=3)(=O)=O)C=CC=CC=1.C(Cl)Cl.N>CO>[CH2:19]([C:18]1[C:13]2[C:12]3[CH:23]=[CH:24][CH:25]=[N:26][C:11]=3[NH:10][C:14]=2[CH:15]=[N:16][C:17]=1[C:21]#[N:22])[CH3:20]

Participants

5

Reactant 3

HCID 222AmmoniaHCID 6344DichloromethaneHCID 582663179-Benzenesulfonyl-5-ethyl-9H-dipyrido[2,3-b;4',3'-d]pyrrole-6-carbonitrile

Product 1

HCID 582664645-Ethyl-9H-dipyrido[2,3-b;4',3'-d]pyrrole-6-carbonitrileYield 81%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 9-benzenesulfonyl-5-ethyl-9H-dipyrido[2,3-b;4′,3′-d]pyrrole-6-carbonitrile (60 mg, 0.16 mmol), DCM (3.0 mL) and 7N ammonia in methanol (3 mL) was stirred at room temperature for 5 days. The reaction mixture was then concentrated in vacuo and the resultant residue was triturated with methanol (2 mL) and dried in vacuo to give the title compound as an off-white solid (28 mg, 81%). LCMS (Method B): RT=2.81 min, M+H+=223.

Workup

  1. concentrationThe reaction mixture was then concentrated in vacuo
  2. customthe resultant residue was triturated with methanol (2 mL)
  3. customdried in vacuo

Sources & evidence

ORD record
ord-c7f4d708981a49df806396e61013919a
Source dataset
uspto-grants-2015_12
Patent number
US09216980B2

Reaction notes

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