1-Isopropylpiperazine → HCID 68682284, compound

HRID 1820549Notes

Reaction equation

HRID 1820549 reaction equation
Cl.[Cl:2][C:3]1[CH:4]=[C:5]([C:22]([OH:24])=O)[CH:6]=[C:7]2[C:11]=1[NH:10][C:9]([C:12]([N:14]1[CH2:19][CH2:18]C(F)(F)[CH2:16][CH2:15]1)=[O:13])=[CH:8]2.ClC1C=C(C(O)=O)C=C2C=1[NH:33][C:32]([C:35](O)=O)=[CH:31]2.[CH:41]([N:44]1[CH2:49][CH2:48][NH:47][CH2:46][CH2:45]1)([CH3:43])[CH3:42].F[B-](F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2C=CC=CC=2N=N1.C(N(CC)C(C)C)(C)C>CN(C)C=O>[Cl:2][C:3]1[CH:4]=[C:5]([C:22]([N:47]2[CH2:48][CH2:49][N:44]([CH:41]([CH3:43])[CH3:42])[CH2:45][CH2:46]2)=[O:24])[CH:6]=[C:7]2[C:11]=1[NH:10][C:9]([C:12]([N:14]1[CH2:15][CH2:16][N:33]([CH:32]([CH3:35])[CH3:31])[CH2:18][CH2:19]1)=[O:13])=[CH:8]2

Participants

7

Reactant 5

HCID 780131-IsopropylpiperazineHCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 68680065HCID 68680065, compound2×HCID 68681331HCID 68681331, compound

Product 1

HCID 68682284HCID 68682284, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The title compounds were synthesized in analogy to example 1, from 7-chloro-2-(4,4-difluoro-piperidine-1-carbonyl)-1H-indole-5-carboxylic acid hydrochloride and 7-chloro-1H-indole-2,5-dicarboxylic acid (intermediate c), 1-isopropylpiperazine (commercially available), O-(benzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium tetrafluoroborate (commercially available) and N,N-diisopropylethylamine in N,N-dimethylformamide. The products were separated by silica gel chromatography using dichloromethane:methanol (19:1 v/v) as eluant.

Workup

  1. customThe products were separated by silica gel chromatography

Sources & evidence

ORD record
ord-24c0ad0fc9344be7be0bdbd5494b41f8
Source dataset
uspto-grants-2009_10
Patent number
US07601711B2

Reaction notes

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