(3S*,4S*)-3-(aminomethyl)-1-azabicyclo[2.2.1]heptan-3-ol dihydrochloride → (3R*,4S*)-N-(thiazolo[5,4-b]pyridin-2-yl)-4'H-1-azaspiro[bicyclo[2.2.1]heptane-3,5'-oxazol]-2'-amine

HRID 2059825Notes

Reaction equation

HRID 2059825 reaction equation
[N:1]1[C:9]2[C:4](=[N:5][CH:6]=[CH:7][CH:8]=2)[S:3][C:2]=1[N:10]=[C:11](SC)SC.Cl.Cl.[NH2:18][CH2:19][C@@:20]1([OH:27])[C@@H:25]2[CH2:26][N:22]([CH2:23][CH2:24]2)[CH2:21]1>>[N:1]1[C:9]2[C:4](=[N:5][CH:6]=[CH:7][CH:8]=2)[S:3][C:2]=1[NH:10][C:11]1[O:27][C@@:20]2([C@@H:25]3[CH2:26][N:22]([CH2:23][CH2:24]3)[CH2:21]2)[CH2:19][N:18]=1

Participants

3

Reactant 2

HCID 57516883(3S*,4S*)-3-(aminomethyl)-1-azabicyclo[2.2.1]heptan-3-ol dihydrochlorideHCID 58088154Dimethyl thiazolo[5,4-b]pyridin-2-ylcarbonimidodithioate

Product 1

HCID 52934202(3R*,4S*)-N-(thiazolo[5,4-b]pyridin-2-yl)-4'H-1-azaspiro[bicyclo[2.2.1]heptane-3,5'-oxazol]-2'-amineYield 67%

Procedure

Dimethyl thiazolo[5,4-b]pyridin-2-ylcarbonimidodithioate and (3S*,4S*)-3-(aminomethyl)-1-azabicyclo[2.2.1]heptan-3-ol dihydrochloride were reacted according to the method of EXAMPLE 4, STEP D to afford (3R*,4S*)—N-(thiazolo[5,4-b]pyridin-2-yl)-4′H-1-azaspiro[bicyclo[2.2.1]heptane-3,5′-oxazol]-2′-amine (87.6 mg, 0.290 mmol, 67% yield). 1H NMR (400 MHz, DMSO-d6) δ ppm 9.16 (br. s., 1H) 8.31 (dd, J=4.77, 1.51 Hz, 1H) 7.90 (dd, J=8.03, 1.51 Hz, 1H) 7.38 (dd, J=8.03, 4.77 Hz, 1H) 4.03 (d, J=10.54 Hz, 1H) 3.81 (d, J=10.54 Hz, 1H) 2.96 (dd, J=13.55, 1.76 Hz, 1H) 2.73-2.88 (m, 3H) 2.61-2.73 (m, 1H) 2.40-2.49 (m, 2H) 1.52-1.70 (m, 1H) 1.25-1.44 (m, 1H). MS(LC/MS) R.T.=0.32; (M+H=302.22).

Sources & evidence

ORD record
ord-de48cb7d54d242be9d0e31c8ad304c40
Source dataset
uspto-grants-2012_10
Patent number
US08278320B2

Reaction notes

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