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Triethylamine → 5-Chloro-N-(6-fluoro-2-oxo-1,2,3,4-tetrahydroquinolin-3-yl)-1H-indole-2-carboxamide

HRID 1376153
Notes
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Reaction equation

HRID 1376153 reaction equation
C(N(CC)CC)C.C1C=CC2N(O)N=NC=2C=1.Cl.[NH2:19][CH:20]1[CH2:29][C:28]2[C:23](=[CH:24][CH:25]=[C:26]([F:30])[CH:27]=2)[NH:22][C:21]1=[O:31].CCN=C=NCCCN(C)C.[Cl:43][C:44]1[CH:45]=[C:46]2[C:50](=[CH:51][CH:52]=1)[NH:49][C:48]([C:53](O)=[O:54])=[CH:47]2>CN(C=O)C.O>[Cl:43][C:44]1[CH:45]=[C:46]2[C:50](=[CH:51][CH:52]=1)[NH:49][C:48]([C:53]([NH:19][CH:20]1[CH2:29][C:28]3[C:23](=[CH:24][CH:25]=[C:26]([F:30])[CH:27]=3)[NH:22][C:21]1=[O:31])=[O:54])=[CH:47]2
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 5

HCID 8471TriethylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 826935-Chloro-1H-indole-2-carboxylic acidHCID 127614113-amino-6-fluoro-3,4-dihydro-2(1H)-quinolinone monohydrochloride

Product 1

HCID 10215557
5-Chloro-N-(6-fluoro-2-oxo-1,2,3,4-tetrahydroquinolin-3-yl)-1H-indole-2-carboxamide
Yield 85%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

Triethylamine (184 μL, 1.32 mmol), HOBt (89 mg, 0.66 mmol), 3-amino-6-fluoro-3,4-dihydro-2(1H)-quinolinone monohydrochloride (CAS Reg. No: 82420-54-0) (143 mg, 0.66 mmol), and EDAC (127 mg, 0.66 mmol) were added to a solution of 5-chloroindole-2-carboxylic acid (129 mg, 0.66 mmol) in anhydrous DMF (3.5 mL). The reaction was stirred at ambient temperature for approximately 16 h, and then poured into water (50 mL). This was stirred vigorously for about 10 mins. and filtered. The collected precipitate was washed with water and dried in vacuum at 40° C., to give the title compound (200 mg, 85%) as an amorphous solid.

Workup

  1. stirringThis was stirred vigorously for about 10 mins
  2. filtrationand filtered
  3. washThe collected precipitate was washed with water
  4. customdried in vacuum at 40° C.

Sources & evidence

ORD record
ord-132b1a1a7b7b4544854944b431453297
Source dataset
uspto-grants-2007_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07169927B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes