1-Cyclohexylpiperazine → HCID 18414476, compound

HRID 1978043Notes

Reaction equation

HRID 1978043 reaction equation
[CH:1]1([N:7]2[CH2:12][CH2:11][NH:10][CH2:9][CH2:8]2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.CC1NC(C)=CC=1[C:19]1[CH:24]=[CH:23][CH:22]=[C:21]([C:25]2[CH:30]=[CH:29][C:28]([CH2:31][C:32](O)=O)=[CH:27][CH:26]=2)[N:20]=1.CSC.B.Cl.[NH2:41]O.[2H]C(Cl)(Cl)Cl.CO[2H]>C(O)C.O1CCCC1>[CH:1]1([N:7]2[CH2:12][CH2:11][N:10]([CH2:32][CH2:31][C:28]3[CH:29]=[CH:30][C:25]([C:21]4[N:20]=[C:19]([NH2:41])[CH:24]=[CH:23][CH:22]=4)=[CH:26][CH:27]=3)[CH2:9][CH2:8]2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

8

Reactant 5

HCID 872981-CyclohexylpiperazineHCID 443297Hydroxyamine hydrochlorideHCID 12423031(Dimethyl sulfide)trihydroboronHCID 54201341HCID 54201341, compoundHCID 131722572HCID 131722572, compound

Product 1

HCID 18414476HCID 18414476, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

Prepared as in Example 112, using N-cyclohexylpiperazine coupling with 2-(2,5-dimethylpyrrolyl)-6-(4-(carboxymethyl)phenyl)-pyridine in 100% yield followed by reduction using borane methyl sulfide in refluxing tetrahydrofuran in 97% yield, then deprotection using hydroxylamine hydrochloride in refluxing ethanol in 98% yield, as the hydrochloride salt.

Workup

  1. customPrepared as in Example 112

Sources & evidence

ORD record
ord-2729e11460ba4ad2b10aede5ffd837ac
Source dataset
uspto-grants-2001_05
Patent number
US06235747B1

Reaction notes

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