Benzyloxyacetyl chloride → HCID 54400812, compound

HRID 1292065Notes

Reaction equation

[C:1]([C:5]1[CH:6]=[C:7]2[N:12]([CH:13]=1)[CH:11]=[CH:10][CH:9]=[CH:8]2)([O:3][CH3:4])=[O:2].[CH2:14]([O:21][CH2:22][C:23](Cl)=[O:24])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>>[CH2:14]([O:21][CH2:22][C:23]([C:13]1[N:12]2[C:7]([CH:8]=[CH:9][CH:10]=[CH:11]2)=[CH:6][C:5]=1[C:1]([O:3][CH3:4])=[O:2])=[O:24])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

Reactant 2

HCID 177085Benzyloxyacetyl chloride

HCID 600232Methyl indolizine-2-carboxylate

Product 1

HCID 54400812HCID 54400812, compound

Procedure

Following the procedure of Example 3, 2-carbomethoxyindolizine was reacted with benzyloxyacetyl chloride to give 3-benzyloxyacetyl-2-carbomethoxyindolizine (VII) Cyclization of VII with hydrazine and reaction of the resulting pyridazino[4,5-b]indolizin-1-one with POCl3 gave the corresponding chloro compound (VIII). The reaction of VII with 4-(2-pyrimidinyl)-1-piperizinyl)ethyl amine gave the title compound. Treatment with ethereal HCl in ether gave the product as the trihydrochloride salt: m.p. 140° C.

Sources & evidence

ORD record: ord-30602f6bc90742fd9f7a2ddf5b7cbc7e
Source dataset: uspto-grants-1998_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05756501

Reaction notes

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