Ammonium Chloride → HCID 178420005, compound

HRID 1772715Notes

Reaction equation

HRID 1772715 reaction equation
[O:1]1[CH2:6][CH2:5][N:4]([C:7]2[C:8]3[N:9]([CH:21]=[C:22]([CH2:24][S:25][C:26]4[CH:35]=[CH:34][C:33]5[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=5)[N:27]=4)[N:23]=3)[C:10]([C:13]3[CH:14]=[CH:15][C:16]([C:19]#[N:20])=[N:17][CH:18]=3)=[CH:11][N:12]=2)[CH2:3][CH2:2]1.[NH4+].[Cl-].[N-:38]=[N+:39]=[N-:40].[Na+]>>[NH:38]1[C:19]([C:16]2[N:17]=[CH:18][C:13]([C:10]3[N:9]4[CH:21]=[C:22]([CH2:24][S:25][C:26]5[CH:35]=[CH:34][C:33]6[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=6)[N:27]=5)[N:23]=[C:8]4[C:7]([N:4]4[CH2:5][CH2:6][O:1][CH2:2][CH2:3]4)=[N:12][CH:11]=3)=[CH:14][CH:15]=2)=[N:20][N:40]=[N:39]1

Participants

4

Reactant 3

HCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 1177277685-(8-Morpholino-2-((quinolin-2-ylthio)methyl)imidazo[1,2-a]pyrazin-5-yl)picolinonitrile

Product 1

HCID 178420005HCID 178420005, compound

Conditions

Temperature
120 °C

Procedure

Compound 75c (54.9 mg, 0.114 mmol) NH4Cl (9.20 mg, 0.172 mmol), and NaN3 (11.2 mg, 0.172 mmol) were placed in an 8 mL vial equipped with a stir bar and then the vial was evacuated and backflushed with Argon gas. Dry DMF (1 mL) was added via syringe and then the mixture was stirred at 120° C. for 2 h. The reaction was cooled to rt, diluted with water (5 mL), and adjusted to pH 2 with 2M HCl. The precipitate was collected by filtration and then the solid was washed with water (2×5 mL). The solid was dissolved in a mixture of DCM (20 mL) and MeOH (10 mL), dried over Na2SO4, and filtered. The solvent was removed under reduced pressure. The residue was triturated with MeOH (5 mL) and the solid was collected by filtration. The residual solvent was removed under reduced pressure to afford the title compound 70. 1H-NMR (400 MHz, DMSO-d6) δ (ppm): 8.98 (s, 1H), 8.30 (s, 2H), 8.17 (d, J=8.6 Hz, 1H), 8.07 (s, 1H), 7.89 (d, J=7.8 Hz, 1H), 7.86 (d, J=8.3 Hz, 1H), 7.66 (t, J=7.6 Hz, 1H), 7.59 (s, 1H), 7.48 (t, J=7.5 Hz, 1H), 7.43 (d, J=8.6 Hz, 1H), 4.68 (s, 2H), 4.15-4.27 (m, 4H), 3.69-3.75 (m, 4H). Mass Spectrum (LCMS, ESI pos.) Calcd. for C26H22N10OS: 523.2 (M+H). found: 523.3.

Workup

  1. customvial equipped with a stir bar
  2. customthe vial was evacuated
  3. additionDry DMF (1 mL) was added via syringe
  4. temperatureThe reaction was cooled to rt
  5. additiondiluted with water (5 mL)
  6. filtrationThe precipitate was collected by filtration
  7. washthe solid was washed with water (2×5 mL)
  8. dissolutionThe solid was dissolved in a mixture of DCM (20 mL) and MeOH (10 mL)
  9. dry with materialdried over Na2SO4
  10. filtrationfiltered
  11. customThe solvent was removed under reduced pressure
  12. customThe residue was triturated with MeOH (5 mL)
  13. filtrationthe solid was collected by filtration
  14. customThe residual solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-3d661b0f662347d48217d62d1f1ea030
Source dataset
uspto-grants-2016_02
Patent number
US09249163B2

Reaction notes

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