Ammonium Chloride → HCID 178470163, compound

HRID 718616Notes

Reaction equation

HRID 718616 reaction equation
[C:1]([C:3]1[N:8]=[CH:7][C:6]([C:9]2[N:13]3[N:14]=[CH:15][CH:16]=[C:17]([N:18]4[CH2:23][CH2:22][O:21][CH2:20][CH2:19]4)[C:12]3=[N:11][C:10]=2[C:24]([O:26][CH2:27][CH3:28])=[O:25])=[CH:5][CH:4]=1)#[N:2].[NH4+].[Cl-].[N-:31]=[N+:32]=[N-:33].[Na+]>>[NH:31]1[C:1]([C:3]2[N:8]=[CH:7][C:6]([C:9]3[N:13]4[N:14]=[CH:15][CH:16]=[C:17]([N:18]5[CH2:19][CH2:20][O:21][CH2:22][CH2:23]5)[C:12]4=[N:11][C:10]=3[C:24]([O:26][CH2:27][CH3:28])=[O:25])=[CH:5][CH:4]=2)=[N:2][N:33]=[N:32]1

Participants

4

Reactant 3

HCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 117728523Ethyl 3-(6-cyanopyridin-3-yl)-8-morpholinoimidazo[1,2-b]pyridazine-2-carboxylate

Product 1

HCID 178470163HCID 178470163, compound

Conditions

Temperature
110 °C

Procedure

Compound 32a (378 mg, 1.00 mmol), NH4Cl (80.2 mg, 1.50 mmol), and NaN3 (97.5 mg, 1.50 mmol) were placed in an 8 mL vial equipped with a stir bar and then the vial was evacuated and backflushed with argon. Dry DMF (4 mL) was added and then the reaction was stirred at 110° C. for 1 h. The reaction was cooled to rt and poured into water (25 mL). The pH of the mixture was adjusted with 2 M HCl to pH 2 and then the precipitate was isolated by filtration. The solid was dried under reduced pressure to afford compound 32b. 1H-NMR (400 MHz, DMSO-d6) δ (ppm): 9.01 (s, 1H), 8.29-8.40 (m, 2H), 8.23 (d, J=5.6 Hz, 1H), 6.50 (d, J=5.6 Hz, 1H), 4.23 (q, J=6.8 Hz, 2H), 4.01-4.11 (m, 4H), 3.77-3.86 (m, 4H), 1.16 (t, J=7.0 Hz, 3H). Mass Spectrum (LCMS, ESI pos.) Calcd. For C19H19N9O3: 422.2 (M+H). Found: 422.2.

Workup

  1. customvial equipped with a stir bar
  2. customthe vial was evacuated
  3. additionDry DMF (4 mL) was added
  4. temperatureThe reaction was cooled to rt
  5. additionpoured into water (25 mL)
  6. customthe precipitate was isolated by filtration
  7. customThe solid was dried under reduced pressure

Sources & evidence

ORD record
ord-aeeba74ba2104c98997e22a20648f870
Source dataset
uspto-grants-2015_11
Patent number
US09193736B2

Reaction notes

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