Isopropyl isocyanate → 4-(3-Bromoimidazo[1,2-b]pyridazin-6-yl)-N-isopropylpiperazine-1-carboxamide

HRID 870760Notes

Reaction equation

HRID 870760 reaction equation
[N:1]([CH:4]([CH3:6])[CH3:5])=[C:2]=[O:3].[Br:7][C:8]1[N:12]2[N:13]=[C:14]([N:17]3[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]3)[CH:15]=[CH:16][C:11]2=[N:10][CH:9]=1>ClCCl>[Br:7][C:8]1[N:12]2[N:13]=[C:14]([N:17]3[CH2:18][CH2:19][N:20]([C:2]([NH:1][CH:4]([CH3:6])[CH3:5])=[O:3])[CH2:21][CH2:22]3)[CH:15]=[CH:16][C:11]2=[N:10][CH:9]=1

Participants

4

Reactant 2

HCID 61277Isopropyl isocyanateHCID 866964323-Bromo-6-piperazin-1-yl-imidazo[1,2-b]pyridazine

Product 1

HCID 866964704-(3-Bromoimidazo[1,2-b]pyridazin-6-yl)-N-isopropylpiperazine-1-carboxamideYield 109.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-Isocyanatopropane [1795-48-8] (120 μL, 1.2 mmol) was added, via syringe, to a stirred, ambient temperature, clear, colorless solution of 3-bromo-6-piperazin-1-yl-imidazo[1,2-b]pyridazine (334.6 mg, 1.2 mmol) in dichloromethane (20 mL). The solution was allowed to proceed for 17 h then evaporated to dryness to afford 481.5 mg of light yellow solid foam. LRMS (ESI) m/z 367.0/369.0 [(M+H)]+, calc'd for C14H19BrN6O: 367.25.

Workup

  1. customthen evaporated to dryness

Sources & evidence

ORD record
ord-e94f7ba7d33f458093e680847647737b
Source dataset
uspto-grants-2015_03
Patent number
US08969565B2

Reaction notes

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