Sodium Phosphate, Dibasic → Tert-butyl (6-iodoimidazo[1,2-b]pyridazin-2-yl)carbamate

HRID 1925110Notes

Reaction equation

[I:1][C:2]1[N:7]=[N:6][C:5]([NH2:8])=[CH:4][CH:3]=1.Cl[CH2:10][C:11]([NH:13][C:14](=[O:20])[O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=O.P([O-])([O-])(O)=O.[Na+].[Na+].CC(N(C)C)=O>O>[I:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([CH:10]=[C:11]([NH:13][C:14](=[O:20])[O:15][C:16]([CH3:19])([CH3:18])[CH3:17])[N:8]=2)[N:7]=1

Participants

Conditions

Temperature: 120 °C

Procedure

A mixture containing compound 7A (2.5 g, 11.3 mmol), tert-butyl 2-chloroacetylcarbamate (2.4 g, 12.4 mmol), sodium hydrogen phosphate (3.2 g, 22.6 mmol) and DMA (23 mL) was heated at 120° C. for two hours. The mixture was cooled to room temperature, poured into a flask containing 400 mL of water and sonicated. The solids were filtered, rinsed with water then dried under vacuum. The solids were then taken up in 600 mL ethyl acetate and filtered over short plug of silica gel. The filtrate was concentrated down to give compound 7B (1.6 g, 39%), as a dark green solid, which was used without further purification. 1H NMR (400 MHz, DMSO-d6) δ ppm 10.21 (br. s., 1 H), 8.06-8.00 (m, 1 H), 7.69 (d, J=9.9 Hz, 1 H), 7.46 (d, J=9.3 Hz, 1 H), 1.48 (s, 9 H) ESI-MS:m/z 361.1 (M+H)+.

Workup

temperatureThe mixture was cooled to room temperature
additionpoured into a flask
customsonicated
filtrationThe solids were filtered
washrinsed with water
customthen dried under vacuum
filtrationfiltered over short plug of silica gel
concentrationThe filtrate was concentrated down

Sources & evidence

ORD record: ord-68f9ea3a43924fa19982700c653faa36
Source dataset: uspto-grants-2012_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08178534B2

Reaction notes

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