3-Isothiocyanatoisoquinoline → (3R,4S)-N-(isoquinolin-3-yl)-4'H-1-azaspiro[bicyclo[2.2.1]heptane-3,5'-oxazol]-2'-amine

HRID 2059824Notes

Reaction equation

[N:1]([C:4]1[N:5]=[CH:6][C:7]2[C:12]([CH:13]=1)=[CH:11][CH:10]=[CH:9][CH:8]=2)=[C:2]=S.Cl.Cl.[NH2:16][CH2:17][C@@:18]1([OH:25])[C@@H:23]2[CH2:24][N:20]([CH2:21][CH2:22]2)[CH2:19]1>>[CH:6]1[C:7]2[C:12](=[CH:11][CH:10]=[CH:9][CH:8]=2)[CH:13]=[C:4]([NH:1][C:2]2[O:25][C@@:18]3([C@@H:23]4[CH2:24][N:20]([CH2:21][CH2:22]4)[CH2:19]3)[CH2:17][N:16]=2)[N:5]=1

Participants

Reactant 2

HCID 574765653-Isothiocyanatoisoquinoline

HCID 57516883(3S*,4S*)-3-(aminomethyl)-1-azabicyclo[2.2.1]heptan-3-ol dihydrochloride

Product 1

HCID 52912200(3R*,4S*)-N-(isoquinolin-3-yl)-4'H-1-azaspiro[bicyclo[2.2.1]heptane-3,5'-oxazol]-2'-amineYield 26%

Procedure

3-Isothiocyanatoisoquinoline and (3S*,4S*)-3-(aminomethyl)-1-azabicyclo[2.2.1]heptan-3-ol dihydrochloride were reacted according to the method of EXAMPLE 6, STEP B to afford (3R*,4S*)—N-(isoquinolin-3-yl)-4′H-1-azaspiro[bicyclo[2.2.1]heptane-3,5′-oxazol]-2′-amine (80 mg, 0.27 mmol, 26% yield).

Sources & evidence

ORD record: ord-137f85e73f2d40b0b50b3cb3124df2db
Source dataset: uspto-grants-2012_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08278320B2

Reaction notes

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