Triethylamine → HCID 67112859, compound

HRID 2284314Notes

Reaction equation

HRID 2284314 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[C:18]3[C:13](=[CH:14][C:15]([NH2:19])=[CH:16][CH:17]=3)[NH:12][CH:11]=2)=[CH:6][CH:5]=1)([O-:3])=[O:2].[CH3:20][N:21]1[C:29]2[C:24](=[CH:25][C:26]([C:30](O)=[O:31])=[CH:27][CH:28]=2)[CH:23]=[CH:22]1.OC1C2N=NNC=2C=CC=1.C(N(CC)CC)C.Cl.C(N=C=NCCCN(C)C)C>CN(C=O)C.O>[CH3:20][N:21]1[C:29]2[C:24](=[CH:25][C:26]([C:30]([NH:19][C:15]3[CH:14]=[C:13]4[C:18]([C:10]([C:7]5[CH:8]=[CH:9][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=5)=[CH:11][NH:12]4)=[CH:17][CH:16]=3)=[O:31])=[CH:27][CH:28]=2)[CH:23]=[CH:22]1

Participants

8

Reactant 5

HCID 8471TriethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 70156011-Methyl-1H-indole-5-carboxylic acidHCID 67112923HCID 67112923, compoundHCID 178418300HCID 178418300, compound

Product 1

HCID 67112859HCID 67112859, compoundYield 57.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 3-(4-nitrophenyl)-1H-indol-6-amine (66.3 mg, 0.26 mmol), 1-methyl-1H-indole-5-carboxylic acid (50.4 mg, 0.29 mmol), hydroxybenzotriazole (3.5 mg, 0.03 mmol) and triethylamine (40.1 μL, 0.29 mmol) in DMF (1.00 mL) was stirred for 5 min before 1-ethyl-3-(3-dimethylaminopropyl) carbodiimide hydrochloride (55.2 mg, 0.29 mmol) was added. The reaction was stirred overnight at room temperature and was then diluted with water (5.0 mL). The precipitate that formed was filtered off and sequentially washed with excess methylene chloride and methanol. The solid was recrystallized using hot methanol and gave a bright yellow solid for 1-methyl-N-(3-(4-nitrophenyl)-1H-indol-6-yl)-1H-indole-5-carboxamide (59.8 mg, 0.15 mmol, 56%) after filtration.

Workup

  1. additionwas added
  2. customThe precipitate that formed
  3. filtrationwas filtered off
  4. washsequentially washed with excess methylene chloride and methanol
  5. customThe solid was recrystallized

Sources & evidence

ORD record
ord-e4cee19fe7fe483b939b90fc29e6afc4
Source dataset
uspto-grants-2015_09
Patent number
US09144557B2

Reaction notes

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