Hydroxyamine hydrochloride → HCID 21995410, compound

HRID 1978042Notes

Reaction equation

HRID 1978042 reaction equation
C(O[C:6]([NH:8][CH:9]1[CH2:14][CH:13]([CH3:15])[NH:12][CH:11]([CH3:16])[CH2:10]1)=O)(C)(C)C.CC1NC(C)=CC=1[C:23]1[CH:28]=[CH:27][CH:26]=[C:25]([C:29]2[CH:34]=[CH:33][C:32]([CH2:35][C:36](O)=O)=[CH:31][CH:30]=2)[N:24]=1.CSC.B.Cl.[NH2:45]O.[2H]C(Cl)(Cl)Cl.CO[2H]>C(O)C.O1CCCC1>[CH3:16][CH:11]1[CH2:10][CH:9]([NH:8][CH3:6])[CH2:14][CH:13]([CH3:15])[N:12]1[CH2:36][CH2:35][C:32]1[CH:33]=[CH:34][C:29]([C:25]2[N:24]=[C:23]([NH2:45])[CH:28]=[CH:27][CH:26]=2)=[CH:30][CH:31]=1

Participants

8

Reactant 5

HCID 443297Hydroxyamine hydrochlorideHCID 12423031(Dimethyl sulfide)trihydroboronHCID 15714114HCID 15714114, compoundHCID 54201341HCID 54201341, compoundHCID 131722572HCID 131722572, compound

Product 1

HCID 21995410HCID 21995410, compoundYield 75%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

Prepared as in Example 112, using 4-t-butoxycarbonylamino-2,6-dimethylpiperidine coupling with 2-(2,5-dimethylpyrrolyl)-6-(4-(carboxymethyl)phenyl)-pyridin in 75% yield, followed by reduction with borane methyl sulfide in refluxing tetrahydrofuran in 17% yield, followed by deprotection using hydroxylamine hydrochloride in refluxing ethanol in 85% yield, as a hygroscopic solid as the hydrochloride salt.

Workup

  1. customPrepared as in Example 112

Sources & evidence

ORD record
ord-51e841a0d0074f45af0dc48464d92b38
Source dataset
uspto-grants-2001_05
Patent number
US06235747B1

Reaction notes

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