Diisopropylethylamine → [3-(3-Bromo-imidazo[1,2-b]pyridazin-6-ylamino)-propyl]-methyl-carbamic acid isopropyl ester

HRID 870674Notes

Reaction equation

HRID 870674 reaction equation
[CH:1]([O:4][C:5](=[O:12])[N:6]([CH2:8][CH2:9][CH2:10][NH2:11])[CH3:7])([CH3:3])[CH3:2].[Br:13][C:14]1[N:18]2[N:19]=[C:20](Cl)[CH:21]=[CH:22][C:17]2=[N:16][CH:15]=1.CCN(C(C)C)C(C)C>>[CH:1]([O:4][C:5](=[O:12])[N:6]([CH2:8][CH2:9][CH2:10][NH:11][C:20]1[CH:21]=[CH:22][C:17]2[N:18]([C:14]([Br:13])=[CH:15][N:16]=2)[N:19]=1)[CH3:7])([CH3:3])[CH3:2]

Participants

4

Reactant 3

HCID 81531DiisopropylethylamineHCID 128723233-Bromo-6-chloroimidazo(1,2-b)pyridazineHCID 61799490(3-Amino-propyl)-methyl-carbamic acid isopropyl ester

Product 1

HCID 86696375[3-(3-Bromo-imidazo[1,2-b]pyridazin-6-ylamino)-propyl]-methyl-carbamic acid isopropyl esterYield 87.1%

Conditions

Temperature
85 °C

Procedure

A stirred mixture of (3-amino-propyl)-methyl-carbamic acid isopropyl ester (3.0 g, 17.0 mmol), 3-bromo-6-chloro-imidazo[1,2-b]pyridazine [13526-66-4] (723.7 mg, 3.1 mmol), and Hunig's base [7087-68-5] (0.6 mL, 3.2 mmol) was heated to 85° C., under N2 blanket, for 3d then preabsorbed on silica gel and flash chromatographed (silica gel eluted with 10% (v/v) methanol/ethyl acetate) to obtain 1.0 g of clear yellow oil. LRMS (ESI) m/z 370.2/372.2 [(M+H)]+, calc'd for C14H20BrN5O2: 370.25.

Workup

  1. customfor 3d then preabsorbed on silica gel and flash
  2. customchromatographed
  3. wash(silica gel eluted with 10% (v/v) methanol/ethyl acetate)

Sources & evidence

ORD record
ord-295ed63273e24be193b914cccdf67346
Source dataset
uspto-grants-2015_03
Patent number
US08969565B2

Reaction notes

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