2-Aminoadamantane → HCID 18414554, compound

HRID 1978045Notes

Reaction equation

HRID 1978045 reaction equation
[NH2:1][CH:2]1[CH:9]2[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:11][CH:3]1[CH2:4]3)[CH2:8]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]>>[CH:9]12[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:11][CH:3]([CH2:4]3)[CH:2]1[NH:1][CH2:31][CH2:30][C:27]1[CH:28]=[CH:29][C:24]([C:20]3[N:19]=[C:18]([NH2:36])[CH:23]=[CH:22][CH:21]=3)=[CH:25][CH:26]=1)[CH2:8]2

Participants

6

Reactant 5

HCID 253322-AminoadamantaneHCID 443297Hydroxyamine hydrochlorideHCID 12423031(Dimethyl sulfide)trihydroboronHCID 54201341HCID 54201341, compoundHCID 131722572HCID 131722572, compound

Product 1

HCID 18414554HCID 18414554, compoundYield 98%

Procedure

Prepared as in Example 112, using 2-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 98% yield, mp 215-230° C. (dec.) as the hydrochloride salt.

Workup

  1. customPrepared as in Example 112

Sources & evidence

ORD record
ord-41062e3e042a4edfbbf6c72638af8484
Source dataset
uspto-grants-2001_05
Patent number
US06235747B1

Reaction notes

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