Triethylamine → N-(6-fluoro-1,2,3,4-tetrahydroquinolin-3-yl)-6H-thieno[2,3-b]pyrrole-5-carboxamide

HRID 1178437Notes

Reaction equation

HRID 1178437 reaction equation
CCN(CC)CC.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.CCN=C=NCCCN(C)C.Cl[C:44]1[S:54][C:47]2[NH:48][C:49]([C:51](O)=[O:52])=[CH:50][C:46]=2[CH:45]=1>CN(C=O)C.O>[F:30][C:26]1[CH:27]=[C:28]2[C:23](=[CH:24][CH:25]=1)[NH:22][CH2:21][CH:20]([NH:19][C:51]([C:49]1[NH:48][C:47]3[S:54][CH:44]=[CH:45][C:46]=3[CH:50]=1)=[O:52])[CH2:29]2

Participants

8

Reactant 5

HCID 8471TriethylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 104428202-Chloro-6H-thieno[2,3-b]pyrrole-5-carboxylic acidHCID 127614113-amino-6-fluoro-3,4-dihydro-2(1H)-quinolinone monohydrochloride

Product 1

HCID 21906824N-(6-fluoro-1,2,3,4-tetrahydroquinolin-3-yl)-6H-thieno[2,3-b]pyrrole-5-carboxamideYield 84%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

Et3N (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 2-chloro-6H-thieno[2,3-b]pyrrole-5-carboxylic acid (133 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 (203 mg, 84%) 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-9474ca54d041461ea6860a8f3fb192b6
Source dataset
uspto-grants-2007_10
Patent number
US07276517B2

Reaction notes

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