Pyridine → N-[(E)-[amino-[3-(quinolin-6-ylmethyl)triazolo[4,5-b]pyrazin-5-yl]methylidene]amino]acetamide

HRID 456137Notes

Reaction equation

HRID 456137 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][C:7]([CH2:11][N:12]3[C:16]4=[N:17][C:18]([C:21](=[N:23][NH2:24])[NH2:22])=[CH:19][N:20]=[C:15]4[N:14]=[N:13]3)=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.N1C=CC=CC=1.[C:31](OC(=O)C)(=[O:33])[CH3:32]>CS(C)=O.C(Cl)Cl>[C:31]([NH:24]/[N:23]=[C:21](\[C:18]1[N:17]=[C:16]2[N:12]([CH2:11][C:7]3[CH:6]=[C:5]4[C:10](=[CH:9][CH:8]=3)[N:1]=[CH:2][CH:3]=[CH:4]4)[N:13]=[N:14][C:15]2=[N:20][CH:19]=1)/[NH2:22])(=[O:33])[CH3:32]

Participants

6

Reactant 3

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 669270911-(Quinolin-6-ylmethyl)-1H-[1,2,3]triazolo[4,5-b]pyrazine-6-carbohydrazonamide

Product 1

HCID 68050620N-[(E)-[amino-[3-(quinolin-6-ylmethyl)triazolo[4,5-b]pyrazin-5-yl]methylidene]amino]acetamideYield 70.6%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 1-(quinolin-6-ylmethyl)-1H-[1,2,3]triazolo[4,5-b]pyrazine-6-carbohydrazonamide (25 mg, 0.078 mmol) in DMSO (1 mL) and DCM (2.0 mL), was added pyridine (6.19 mg, 0.078 mmol) and acetic anhydride (10.39 mg, 0.102 mmol). After stirring overnight, the reaction mixture was filtered. The solid was washed with EtOH, H2O and EtOH to give 19.9 mg of title compound in 67% yield. 1H-NMR (400 MHz, DMSO-d6) δ ppm 9.48 (d, 1H), 8.88 (d, 1H), 8.34 (d, 1H), 8.05 (s, 1H), 8.01 (d, 1H), 7.86 (d, 1H), 7.53 (dd, 1H), 6.20 (s, 2H), 2.24 (s, 1H), 2.00 (s, 1H). LCMS (method B): [MH]+=362, tR=1.60 min.

Workup

  1. filtrationthe reaction mixture was filtered
  2. washThe solid was washed with EtOH, H2O and EtOH

Sources & evidence

ORD record
ord-e6a9bb4bdd1e417e9990b4188a472ba5
Source dataset
uspto-grants-2013_07
Patent number
US08497368B2

Reaction notes

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