Hydrochloric Acid → 3-(5-Phenyl-1,3,4-oxadiazol-2-yl)-5-(2,7-diazaspiro[4.4]nonan-2-yl)pyrazin-2-amine

HRID 1959449Notes

Reaction equation

HRID 1959449 reaction equation
C(OC([N:8](C(OC(C)(C)C)=O)[C:9]1[N:10]=[CH:11][C:12]([N:26]2[CH2:41][CH2:40][C:28]3([CH2:32][CH2:31][N:30](C(OC(C)(C)C)=O)[CH2:29]3)[CH2:27]2)=[N:13][C:14]=1[C:15]1[O:16][C:17]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[N:18][N:19]=1)=O)(C)(C)C.Cl>O1CCOCC1>[C:20]1([C:17]2[O:16][C:15]([C:14]3[C:9]([NH2:8])=[N:10][CH:11]=[C:12]([N:26]4[CH2:41][CH2:40][C:28]5([CH2:32][CH2:31][NH:30][CH2:29]5)[CH2:27]4)[N:13]=3)=[N:19][N:18]=2)[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 66744439Tert-butyl 7-[5-[bis(tert-butoxycarbonyl)amino]-6-(5-phenyl-1,3,4-oxadiazol-2-yl)pyrazin-2-yl]-3,7-diazaspiro[4.4]nonane-3-carboxylate

Product 1

HCID 667445763-(5-Phenyl-1,3,4-oxadiazol-2-yl)-5-(2,7-diazaspiro[4.4]nonan-2-yl)pyrazin-2-amine

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

tert-Butyl 7-[5-[bis(tert-butoxycarbonyl)amino]-6-(5-phenyl-1,3,4-oxadiazol-2-yl)pyrazin-2-yl]-3,7-diazaspiro[4.4]nonane-3-carboxylate (50.9 mg, 0.07668 mmol) was treated with a solution of hydrogen chloride (192 μL, of 4 M, 0.77 mmol) in dioxane. The reaction mixture was stirred for 2 h at room temperature. The solvent was removed under reduced pressure and the residue was dissolved in DMF and purified by reverse phase HPLC using (1-99% ACN/H2O (5 mM HCl)) to yield 3-(5-phenyl-1,3,4-oxadiazol-2-yl)-5-(2,7-diazaspiro[4.4]nonan-2-yl)pyrazin-2-amine. 1H NMR (400 MHz, DMSO-d6) δ 9.34 (s, 2H), 8.25-7.99 (m, 2H), 7.89 (s, 1H), 7.66 (d, J=6.6 Hz, 3H), 3.60-3.47 (m, 4H); 3.36-3:25 (m, 2H), 3.18 (tt, J=12.1, 6.0 Hz, 2H), 2.19-1.83 (m, J=17.8, 12.7, 5.9 Hz, 4H); LC/MS m/z 364.1 [M+H]+.

Workup

  1. customThe solvent was removed under reduced pressure
  2. dissolutionthe residue was dissolved in DMF
  3. custompurified by reverse phase HPLC

Sources & evidence

ORD record
ord-84849ad74556432abdfe0e93af131e7b
Source dataset
uspto-grants-2013_04
Patent number
US08410112B2

Reaction notes

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