Triethylamine → HCID 178512573, compound

HRID 1192238Notes

Reaction equation

HRID 1192238 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]([C:11]2[S:12][C:13]([S:19][C:20]3[C:25]([Cl:26])=[CH:24][N:23]=[CH:22][C:21]=3[Cl:27])=[C:14]([N+:16]([O-:18])=[O:17])[CH:15]=2)=[O:10])=[CH:4][CH:3]=1.Cl.[N:29]1([C:38](=N)[NH2:39])C2C=CC=CC=2N=N1.C(N(CC)CC)C>C(#N)C>[Cl:26][C:25]1[CH:24]=[N:23][CH:22]=[C:21]([Cl:27])[C:20]=1[S:19][C:13]1[S:12][C:11]([C:9]([NH:8][C:5]2[CH:4]=[CH:3][C:2]([NH:1][C:38]([NH2:39])=[NH:29])=[CH:7][CH:6]=2)=[O:10])=[CH:15][C:14]=1[N+:16]([O-:18])=[O:17]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 534349021H-Benzotriazole-1-carboximidamide--hydrogen chloride (1/1)HCID 60207458HCID 60207458, compound

Product 1

HCID 178512573HCID 178512573, compoundYield 9.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of N-(4-aminophenyl)-5-((3,5-dichloropyridin-4-yl)thio)-4-nitrothiophene-2-carboxamide (0.2 g, 0.45 mmol) and 1H-benzo[d][1,2,3]triazole-1-carboximidamide HCl salt (0.18 g, 0.91 mmol) in acetonitrile (4 mL) was added triethylamine (0.13 mL, 0.91 mmol). After the addition, the resulting reaction mixture was heated at 60° C. for 24 hours. After this time, the reaction mixture was concentrated and purified by reverse phase HPLC to afford the titled product as a solid (20 mg, 9% yield). 1H NMR (400 MHz, d6-DMSO) δ: 10.66 (1H, s), 9.68 (1H, m), 9.01 (2H, m), 8.74 (1H, s), 7.73 (2H, m), 7.39 (4H, m), 7.25 (3H, m), 7.12 (2H, dd). MS m/z: 483.06, 485.06 [M+H]+.

Workup

  1. additionAfter the addition
  2. customthe resulting reaction mixture
  3. concentrationAfter this time, the reaction mixture was concentrated
  4. custompurified by reverse phase HPLC

Sources & evidence

ORD record
ord-7c1edaf4d87644c790604b52360ed3bb
Source dataset
uspto-grants-2014_03
Patent number
US08680139B2

Reaction notes

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