Triethylamine → HCID 16202226, compound

HRID 1663243Notes

Reaction equation

HRID 1663243 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([S:9]([N:12]2[CH:25]([CH2:26][C:27](O)=[O:28])[C:24]3[C:19](=[CH:20][CH:21]=[C:22]([F:30])[CH:23]=3)[C:18]3[CH:17]=[CH:16][CH:15]=[CH:14][C:13]2=3)(=[O:11])=[O:10])[CH:5]=[CH:6][C:7]=1[Cl:8].C(N(CC)CC)C.Cl.CN(C)CCCN=C=NCC.Cl.Cl.[NH:52]1[CH2:56][CH2:55][N:54]=[C:53]1[C:57]1[CH:62]=[CH:61][C:60]([CH2:63][CH2:64][NH2:65])=[CH:59][CH:58]=1>CN(C)C=O>[ClH:1].[Cl:1][C:2]1[CH:3]=[C:4]([S:9]([N:12]2[CH:25]([CH2:26][C:27]([NH:65][CH2:64][CH2:63][C:60]3[CH:61]=[CH:62][C:57]([C:53]4[NH:54][CH2:55][CH2:56][N:52]=4)=[CH:58][CH:59]=3)=[O:28])[C:24]3[C:19](=[CH:20][CH:21]=[C:22]([F:30])[CH:23]=3)[C:18]3[CH:17]=[CH:16][CH:15]=[CH:14][C:13]2=3)(=[O:10])=[O:11])[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

6

Reactant 4

HCID 8471Triethylamine2×HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 67217405HCID 67217405, compoundHCID 67437256HCID 67437256, compound

Product 1

HCID 16202226HCID 16202226, compoundYield 251.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of [5-(3,4-dichloro-benzenesulfonyl)-8-fluoro-5,6-dihydro-phenanthridin-6-yl]-acetic acid (210 mg, 0.45 mmol), triethylamine (0.07 mL, 1.5 mmol) and N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (0.19 g, 0.5 mmol) in dry dimethyl formamide (5 mL) was stirred at room temperature for five minutes before 2-[4-(4,5-dihydro-1H-imidazol-2-yl)-phenyl]-ethylamine dihydrochloride (Reference Example 2) (131 mg, 0.5 mmol) was added. The pH of the reaction mixture was adjusted to 8 by addition of triethylamine, the so obtained mixture was stirred at room temperature overnight, then concentrated in vacuo. The residue was purified by preparative thin-layer chromatography (dichloromethane:methanol:NH4OH=5:1:0.1) to yield 382 mg (75%) of the title compound as white crystals.

Workup

  1. additionwas added
  2. concentrationconcentrated in vacuo
  3. customThe residue was purified by preparative thin-layer chromatography (dichloromethane:methanol:NH4OH=5:1:0.1)

Sources & evidence

ORD record
ord-a0aecb5ebc8e45ea93f644ea3ebe37ee
Source dataset
uspto-grants-2011_10
Patent number
US08034827B2

Reaction notes

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