Ethanolamine → HCID 59233136, compound

HRID 1925122Notes

Reaction equation

HRID 1925122 reaction equation
Cl.[I:2][C:3]1[CH:4]=[CH:5][C:6]2[N:7]([CH:9]=[C:10]([NH2:12])[N:11]=2)[N:8]=1.Cl[C:14](OC1C=CC(C(OC)=O)=CC=1)=[O:15].[CH2:27]([CH2:29][NH2:30])[OH:28]>CN(C1C=CN=CC=1)C.C(Cl)Cl>[OH:28][CH2:27][CH2:29][NH:30][C:14]([NH:12][C:10]1[N:11]=[C:6]2[CH:5]=[CH:4][C:3]([I:2])=[N:8][N:7]2[CH:9]=1)=[O:15]

Participants

6

Reactant 3

HCID 700EthanolamineHCID 854163Methyl 4-[(chlorocarbonyl)oxy]benzoateHCID 86639817HCID 86639817, compound

Product 1

HCID 59233136HCID 59233136, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
25 °C

Procedure

To a solution of 6-iodoimidazo[1,2-b]pyridazin-2-amine hydrochloride (250 mg, 0.843 mmol) and DMAP (227 mg, 1.855 mmol) in DCM (Volume: 5.0 mL) was added methyl 4-(chlorocarbonyloxy)benzoate (199 mg, 0.927 mmol) at 25° C. The reaction was stirred at 25° C. for 1 hr to provide a dark green heterogeneous mixture which was filtered. The solid was resuspended in DCM (Volume: 5.0 mL), treated with ethanolamine (2M in MeOH, 0.843 mL, 1.686 mmol) at room temperature, and then stirred for an additional 1 hr. The reaction was then evaporated to dryness via rotary evaporation, and the resulting residue was suspended in EtOAc (Volume: 10.0 mL). The mixture was filtered, and the resulting black solid was dried under high vacuum and used without further purification.

Workup

  1. customto provide a dark green heterogeneous mixture which
  2. filtrationwas filtered
  3. stirringstirred for an additional 1 hr
  4. customThe reaction was then evaporated to dryness via rotary evaporation
  5. filtrationThe mixture was filtered
  6. customthe resulting black solid was dried under high vacuum
  7. customused without further purification

Sources & evidence

ORD record
ord-0d0e0e36fa354325b0445973db45a8d1
Source dataset
uspto-grants-2012_05
Patent number
US08178534B2

Reaction notes

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