Ammonium formate → Ethyl 2-(8-morpholinoimidazo[1,2-b]pyridazin-2-yl)acetate

HRID 718608Notes

Reaction equation

Cl[C:2]1[CH:3]=[C:4]([N:17]2[CH2:22][CH2:21][O:20][CH2:19][CH2:18]2)[C:5]2[N:6]([CH:8]=[C:9]([CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])[N:10]=2)[N:7]=1.C([O-])=O.[NH4+]>C(Cl)Cl.[Pd]>[O:20]1[CH2:19][CH2:18][N:17]([C:4]2[C:5]3[N:6]([CH:8]=[C:9]([CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])[N:10]=3)[N:7]=[CH:2][CH:3]=2)[CH2:22][CH2:21]1

Participants

Conditions

Temperature: 70 °C

Procedure

Compound 28b (1.00 g, 3.08 mmol) and 10% Pd on activated carbon (164 mg, 0.154 mmol) were placed in a 40 mL vial equipped with a stir bar and then the vial was evacuated and backflushed with argon. Dry THF (10 mL) was added followed by ammonium formate (388 mg, 6.16 mmol) and then the reaction was stirred at 70° C. for 1 h. The reaction was cooled to rt and diluted with DCM (200 mL). The solids were removed by filtration and then washed with DCM (2×50 mL). The combined filtrates were concentrated under reduced pressure to afford compound 28c. 1H-NMR (400 MHz, CDCl3) δ (ppm): 7.96 (d, J=5.1 Hz, 1H), 7.80 (s, 1H), 6.02 (d, J=5.1 Hz, 1H), 4.21 (q, J=6.8 Hz, 2H), 3.85-4.01 (m, 8H), 3.83 (s, 2H), 1.29 (t, J=6.8 Hz, 3H). Mass Spectrum (LCMS, ESI pos.) Calcd. For C14H18N4O3: 291.2 (M+H). Found: 291.1.

Workup

customvial equipped with a stir bar
customthe vial was evacuated
additionDry THF (10 mL) was added
temperatureThe reaction was cooled to rt
customThe solids were removed by filtration
washwashed with DCM (2×50 mL)
concentrationThe combined filtrates were concentrated under reduced pressure

Sources & evidence

ORD record: ord-6546fc4ef6b04e9fac9dfa8eb7f59682
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09193736B2

Reaction notes

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