Hydrochloric Acid → HCID 136338253, compound

HRID 1529432Notes

Reaction equation

HRID 1529432 reaction equation
[CH:1]([O:4][C:5]1[N:10]=[C:9]([C:11]2[CH:12]=[C:13]3[C:17](=[CH:18][CH:19]=2)[NH:16][CH:15]=[C:14]3[C:20]2[O:24][C:23]([N:25]3[CH2:30][CH2:29][CH:28]([NH:31]C(=O)OC(C)(C)C)[CH2:27][CH2:26]3)=[N:22][N:21]=2)[CH:8]=[N:7][CH:6]=1)([CH3:3])[CH3:2].Cl>CO>[CH:1]([O:4][C:5]1[N:10]=[C:9]([C:11]2[CH:12]=[C:13]3[C:17](=[CH:18][CH:19]=2)[NH:16][CH:15]=[C:14]3[C:20]2[O:24][C:23]([N:25]3[CH2:26][CH2:27][CH:28]([NH2:31])[CH2:29][CH2:30]3)=[N:22][N:21]=2)[CH:8]=[N:7][CH:6]=1)([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 136338252HCID 136338252, compound

Product 1

HCID 136338253HCID 136338253, compoundYield 31.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To a solution of tert-butyl (1-(5-(5-(6-isopropoxypyrazin-2-yl)-1H-indol-3-yl)-1,3,4-oxadiazol-2-yl)piperidin-4-yl)carbamate (80 mg, 0.15 mmol) in MeOH (1 mL) was added HCl in MeOH (2 mL) and the reaction was stirred for 4 h at RT. The suspension was filtered and the filtrate was washed with Et2O and basified with saturated NaHCO3 solution. The mixture was extracted in EtOAc (2×3 mL). The combined organic layer were dried over anhydrous Na2SO4, filtered and concentrated. The residue was triturated with 10% EtOAc in petroleum ether to give 1-(5-(5-(6-isopropoxypyrazin-2-yl)-1H-indol-3-yl)-1,3,4-oxadiazol-2-yl)piperidin-4-amine (20 mg, 31.2%) as a solid. MS (ESI, pos. ion) m/z: 420.3 (M+1); 1H NMR (400 MHz, DMSO-d6): δ ppm 8.73 (s, 1H), 7.96-8.13 (m, 3H), 7.63 (d, J=7.6 Hz, 1H), 5.42 (brs, 1H), 3.90 (d, J=10.8 Hz, 3H), 3.13-3.18 (m, 2H), 2.80 (brs, 2H), 1.82 (d, J=10.4 Hz, 3H), 1.23-1.50 (s, 8H).

Workup

  1. filtrationThe suspension was filtered
  2. washthe filtrate was washed with Et2O and basified with saturated NaHCO3 solution
  3. extractionThe mixture was extracted in EtOAc (2×3 mL)
  4. dry with materialThe combined organic layer were dried over anhydrous Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was triturated with 10% EtOAc in petroleum ether

Sources & evidence

ORD record
ord-e8f7db8e90d747638a806526699835da
Source dataset
uspto-grants-2015_07
Patent number
US09090593B2

Reaction notes

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