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Hydrazine → N-{4-[4-(4-chlorobenzyl)-3-cyano-5-(4H-1,2,4-triazol-3-yl)-2-thienyl]pyridin-2-yl}acetamide

HRID 2401716
Notes
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Reaction equation

HRID 2401716 reaction equation
[C:1]([NH:4][C:5]1[CH:10]=[C:9]([C:11]2[S:15][C:14]([C:16]([NH2:18])=O)=[C:13]([CH2:19][C:20]3[CH:25]=[CH:24][C:23]([Cl:26])=[CH:22][CH:21]=3)[C:12]=2[C:27]#[N:28])[CH:8]=[CH:7][N:6]=1)(=[O:3])[CH3:2].COC(OC)[N:32]([CH3:34])C.[NH2:37]N>C1(C)C=CC=CC=1>[Cl:26][C:23]1[CH:22]=[CH:21][C:20]([CH2:19][C:13]2[C:12]([C:27]#[N:28])=[C:11]([C:9]3[CH:8]=[CH:7][N:6]=[C:5]([NH:4][C:1](=[O:3])[CH3:2])[CH:10]=3)[S:15][C:14]=2[C:16]2[NH:18][CH:34]=[N:32][N:37]=2)=[CH:25][CH:24]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 9321HydrazineHCID 78373Dimethylformamide dimethyl acetalHCID 667479905-[2-(Acetylamino)pyridin-4-yl]-3-(4-chlorobenzyl)-4-cyanothiophene-2-carboxamide

Product 1

HCID 178474072N-{4-[4-(4-chlorobenzyl)-3-cyano-5-(4H-1,2,4-triazol-3-yl)-2-thienyl]pyridin-2-yl}acetamideYield 50.4%

Reagents, catalysts & solvents 1

HCID 1140
Toluene
Solvent

Conditions

Temperature
100 °C

Procedure

To a solution of 5-[2-(acetylamino)pyridin-4-yl]-3-(4-chlorobenzyl)-4-cyanothiophene-2-carboxamide (0.030 g, 0.073 mmol) in toluene (0.75 mL) was added 1,1-dimethoxy-N,N-dimethylmethanamine (0.0970 mL, 0.730 mmol), and the mixture was stirred at 100° C. for 90 minutes. The mixture was concentrated and the residue was dissolved in acetic acid (0.75 mL). Hydrazine (0.0114 mL, 0.365 mmol) was added and the mixture was stirred at 100° C. for 1 hour. The mixture was concentrated and the residue was treated with water. The precipitate was collected, washed with water and dried in a vacuum oven to yield the title compound (0.016 g, 48%). LCMS: (FA) ES+, 435. 1H NMR (400 MHz, d6-DMSO) δ: 10.76 (s, 1H), 8.77 (s, 1H), 8.54-8.46 (m, 2H), 7.50-7.47 (m, 1H), 7.37-7.26 (m, 4H), 4.63 (s, 2H), 2.12 (s, 3H).

Workup

  1. concentrationThe mixture was concentrated
  2. dissolutionthe residue was dissolved in acetic acid (0.75 mL)
  3. stirringthe mixture was stirred at 100° C. for 1 hour
  4. concentrationThe mixture was concentrated
  5. additionthe residue was treated with water
  6. customThe precipitate was collected
  7. washwashed with water
  8. customdried in a vacuum oven

Sources & evidence

ORD record
ord-83cfb543a2dd4f369be8c3fec470e53a
Source dataset
uspto-grants-2014_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08796268B2

Reaction notes

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