Hydrochloric Acid → 1-(7-(5-Amino-6-(5-(4-((methylamino)methyl)phenyl)-1,3,4-oxadiazol-2-yl)pyrazin-2-yl)-2,7-diazaspiro[4.4]nonan-2-yl)propan-1-one

HRID 1959455Notes

Reaction equation

HRID 1959455 reaction equation
C(OC([N:8](C(OC(C)(C)C)=O)[C:9]1[C:10]([C:28]2[O:32][C:31]([C:33]3[CH:38]=[CH:37][C:36]([CH2:39][N:40](C)[C:41](=O)OC(C)(C)C)=[CH:35][CH:34]=3)=[N:30][N:29]=2)=[N:11][C:12]([N:15]2[CH2:27][CH2:26][C:17]3([CH2:21][CH2:20][N:19]([C:22](=[O:25])[CH2:23][CH3:24])[CH2:18]3)[CH2:16]2)=[CH:13][N:14]=1)=O)(C)(C)C.Cl>O1CCOCC1>[NH2:8][C:9]1[N:14]=[CH:13][C:12]([N:15]2[CH2:27][CH2:26][C:17]3([CH2:18][N:19]([C:22](=[O:25])[CH2:23][CH3:24])[CH2:20][CH2:21]3)[CH2:16]2)=[N:11][C:10]=1[C:28]1[O:32][C:31]([C:33]2[CH:38]=[CH:37][C:36]([CH2:39][NH:40][CH3:41])=[CH:35][CH:34]=2)=[N:30][N:29]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 66744380HCID 66744380, compound

Product 1

HCID 667444791-(7-(5-Amino-6-(5-(4-((methylamino)methyl)phenyl)-1,3,4-oxadiazol-2-yl)pyrazin-2-yl)-2,7-diazaspiro[4.4]nonan-2-yl)propan-1-one

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

A solution of tert-butyl N-[[4-[5-[3-[bis(tert-butoxycarbonyl)amino]-6-(3-propanoyl-3,7-diazaspiro[4.4]nonan-7-yl)pyrazin-2-yl]-1,3,4-oxadiazol-2-yl]phenyl]methyl]-N-methyl-carbamate (129 mg, 0.17 mmol) in dioxane (0.3 mL) was treated with a solution of hydrogen chloride (423 μL of 4 M, 1.7 mmol) in dioxane and the reaction mixture was allowed to stir for 40 minutes. The solvents were removed under reduced pressure and the residue was dissolved in DMF (1 mL) and purified by reverse phase HPLC using (10-99% ACN/H2O (5 mM HCl modifier)) to yield 1-(7-(5-amino-6-(5-(4-((methylamino)methyl)phenyl)-1,3,4-oxadiazol-2-yl)pyrazin-2-yl)-2,7-diazaspiro[4.4]nonan-2-yl)propan-1-one. 1H NMR (400 MHz, DMSO-d6) d 9.44 (s, 2H), 8.13 (dd, J=8.3, 2.4 Hz, 2H), 7.91 (t, J=4.5 Hz, 1H), 7.81 (d, J=7.5 Hz, 2H), 4.26-4.20 (m, 2H), 3.58 (dt, J=13.6, 6.8 Hz, 3H), 3.51-3.29 (m, 5H), 2.57 (t, J=5.3 Hz, 3H), 2.24 (dt, J=15.1, 7.5 Hz, 2H), 1.94 (ddt, J=32.7, 13.2, 6.6 Hz, 4H), 0.99 (dd, J=16.5, 7.5 Hz, 3H). LC/MS m/z 463.5 [M+H]+.

Workup

  1. customThe solvents were removed under reduced pressure
  2. dissolutionthe residue was dissolved in DMF (1 mL)
  3. custompurified by reverse phase HPLC

Sources & evidence

ORD record
ord-db6e2c370ceb4d22adacd0bc515acafa
Source dataset
uspto-grants-2013_04
Patent number
US08410112B2

Reaction notes

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