Hydrochloric Acid → [5-(4-Isopropyl-piperazine-1-carbonyl)-1H-indol-2-yl]-(4-methyl-piperidin-1-yl)-methanone

HRID 1820339Notes

Reaction equation

HRID 1820339 reaction equation
[CH:1]([N:4]1[CH2:9][CH2:8][N:7]([C:10]([C:12]2[CH:13]=[C:14]3[C:18](=[CH:19][CH:20]=2)[NH:17][C:16]([C:21]([OH:23])=O)=[CH:15]3)=[O:11])[CH2:6][CH2:5]1)([CH3:3])[CH3:2].Cl.F[B-](F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2C=CC=CC=2N=N1.[CH3:47][CH:48]1[CH2:53][CH2:52][NH:51][CH2:50][CH2:49]1.C(N(CC)C(C)C)(C)C>CN(C)C=O>[CH:1]([N:4]1[CH2:5][CH2:6][N:7]([C:10]([C:12]2[CH:13]=[C:14]3[C:18](=[CH:19][CH:20]=2)[NH:17][C:16]([C:21]([N:51]2[CH2:52][CH2:53][CH:48]([CH3:47])[CH2:49][CH2:50]2)=[O:23])=[CH:15]3)=[O:11])[CH2:8][CH2:9]1)([CH3:3])[CH3:2]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 693814-MethylpiperidineHCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 685341205-(4-isopropyl-piperazine-1-carbonyl)-1H-indole-2-carboxylic acid

Product 1

HCID 68680243[5-(4-Isopropyl-piperazine-1-carbonyl)-1H-indol-2-yl]-(4-methyl-piperidin-1-yl)-methanone

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The title compound was synthesized in analogy to example 1, from 5-(4-isopropyl-piperazine-1-carbonyl)-1H-indole-2-carboxylic acid 1:1 hydrochloride, O-(benzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium tetrafluoroborate (commercially available), 4-methyl piperidine (commercially available) and N,N-diisopropylethylamine in N,N-dimethylformamide to give the desired product after purification by preparative HPLC on reversed phase eluting with a gradient formed from acetonitrile/water/formic acid.

Sources & evidence

ORD record
ord-da817dd833f448809a9e14d885fd644b
Source dataset
uspto-grants-2009_10
Patent number
US07601711B2

Reaction notes

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