Triethylamine → HCID 22496377, compound

HRID 1816174Notes

Reaction equation

HRID 1816174 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]([CH2:21][C:22]2[CH:30]=[CH:29][C:25]([C:26]([OH:28])=O)=[CH:24][CH:23]=2)[C:9]2[S:10][CH:11]=[C:12]([C:14]3[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][CH:15]=3)[N:13]=2)=[CH:4][CH:3]=1.ON1C2C=CC=CC=2N=N1.Cl.C(N=C=NCCCN(C)C)C.C(N(CC)CC)C.O.[NH2:61][C:62]1[NH:66][N:65]=[N:64][N:63]=1>CN(C=O)C.O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]([CH2:21][C:22]2[CH:30]=[CH:29][C:25]([C:26]([NH:61][C:62]3[N:63]=[N:64][NH:65][N:66]=3)=[O:28])=[CH:24][CH:23]=2)[C:9]2[S:10][CH:11]=[C:12]([C:14]3[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][CH:15]=3)[N:13]=2)=[CH:6][CH:7]=1

Participants

8

Reactant 5

HCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 22496522HCID 22496522, compoundHCID 178509300HCID 178509300, compound

Product 1

HCID 22496377HCID 22496377, compoundYield 84.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

4-({(4-Chlorophenyl)-[4-(4-chlorophenyl)thiazol-2-yl]amino}methyl)benzoic acid (0.15 g, 0.33 mmol) was dissolved in DMF (5 mL) and 1-hydroxybenzotriazol (49 mg, 0.36 mmol), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (69 mg, 0.36 mmol), and triethylamine (51 μL, 0.36 mmol) were added and the resulting mixture was stirred at room temperature for 15 minutes. 5-Aminotetrazole hydrate (34 mg, 0.33 mmol) was added and the resulting mixture was stirred at room temperature for 16 hours. Water was added and the mixture was stirred at room temperature for 1 hour and filtered. Washing with water and drying in vacuo afforded 145 mg (84%) of the title compound as a solid.

Workup

  1. stirringthe resulting mixture was stirred at room temperature for 16 hours
  2. stirringthe mixture was stirred at room temperature for 1 hour
  3. filtrationfiltered
  4. washWashing with water
  5. customdrying in vacuo

Sources & evidence

ORD record
ord-068e9193387b44f4b8d9881447f45eea
Source dataset
uspto-grants-2005_04
Patent number
US06881746B2

Reaction notes

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