Amantadine → HCID 18414489, compound

HRID 1978044Notes

Reaction equation

HRID 1978044 reaction equation
[NH2:1][C:2]12[CH2:11][CH:6]3[CH2:7][CH:8]([CH2:10][CH:4]([CH2:5]3)[CH2:3]1)[CH2:9]2.CC1NC(C)=CC=1[C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([C:24]2[CH:29]=[CH:28][C:27]([CH2:30][C:31](O)=O)=[CH:26][CH:25]=2)[N:19]=1.Cl.[NH2:36]O.CSC.B.[2H]C(Cl)(Cl)Cl.CO[2H]>>[C:2]12([NH:1][CH2:31][CH2:30][C:27]3[CH:28]=[CH:29][C:24]([C:20]4[N:19]=[C:18]([NH2:36])[CH:23]=[CH:22][CH:21]=4)=[CH:25][CH:26]=3)[CH2:3][CH:4]3[CH2:10][CH:8]([CH2:7][CH:6]([CH2:5]3)[CH2:11]1)[CH2:9]2

Participants

6

Reactant 5

HCID 2130AmantadineHCID 443297Hydroxyamine hydrochlorideHCID 12423031(Dimethyl sulfide)trihydroboronHCID 54201341HCID 54201341, compoundHCID 131722572HCID 131722572, compound

Product 1

HCID 18414489HCID 18414489, compoundYield 89.5%

Procedure

Preparedas in Example 112, using 1-aminoadamantane for the coupling with 2-(2,5-dimethylpyrrolyl)-6-(4-(carboxymethyl)phenyl)-pyridine followed by deblocking with hydroxylamine hydrochloride and borane methyl sulfide reduction in 89.5% yield, mp 200-220° C. (dec.) as the hydrochloride salt.

Sources & evidence

ORD record
ord-3ae96c0e7ac848c5918aa6eef265b877
Source dataset
uspto-grants-2001_05
Patent number
US06235747B1

Reaction notes

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