2-Fluoroaniline → 5-(4-Cyclopentyl-piperazine-1-carbonyl)-1H-indole-2-carboxylic acid (2-fluoro-phenyl)-amide

HRID 1820357Notes

Reaction equation

HRID 1820357 reaction equation
[CH:1]1([N:6]2[CH2:11][CH2:10][N:9]([C:12]([C:14]3[CH:15]=[C:16]4[C:20](=[CH:21][CH:22]=3)[NH:19][C:18]([C:23](O)=[O:24])=[CH:17]4)=[O:13])[CH2:8][CH2:7]2)[CH2:5][CH2:4][CH2:3][CH2:2]1.C1(N2CCN(C(C3C=C4C(=CC=3)NC(C(N3CCS(=O)(=O)CC3)=O)=C4)=O)CC2)CCCC1.F[B-](F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2C=CC=CC=2N=N1.[F:80][C:81]1[CH:87]=[CH:86][CH:85]=[CH:84][C:82]=1[NH2:83].C(N(CC)C(C)C)(C)C>CN(C)C=O>[F:80][C:81]1[CH:87]=[CH:86][CH:85]=[CH:84][C:82]=1[NH:83][C:23]([C:18]1[NH:19][C:20]2[C:16]([CH:17]=1)=[CH:15][C:14]([C:12]([N:9]1[CH2:8][CH2:7][N:6]([CH:1]3[CH2:2][CH2:3][CH2:4][CH2:5]3)[CH2:11][CH2:10]1)=[O:13])=[CH:22][CH:21]=2)=[O:24]

Participants

7

Reactant 5

HCID 95842-FluoroanilineHCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 68680722[5-(4-Cyclopentyl-piperazine-1-carbonyl)-1H-indol-2-yl]-(1,1-dioxo-thiomorpholin-4-yl)-methanone2×HCID 68681770HCID 68681770, compound

Product 1

HCID 866158055-(4-Cyclopentyl-piperazine-1-carbonyl)-1H-indole-2-carboxylic acid (2-fluoro-phenyl)-amideYield 6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The title compound was synthesized in analogy to example 1, from 5-(4-cyclopentyl-piperazine-1-carbonyl)-1H-indole-2-carboxylic acid 1:1 hydrochloride (example 34, intermediate b), O-(benzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium tetrafluoroborate (commercially available), 2-fluoroaniline (commercially available) and N,N-diisopropylethylamine in N,N-dimethylformamide, to give the desired product as a light yellow solid (6%).

Sources & evidence

ORD record
ord-a86cbc8c89734872a928193f4956aed4
Source dataset
uspto-grants-2009_10
Patent number
US07601711B2

Reaction notes

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