N,N-Dimethylethylenediamine → 3-((6-Chloro-3-cyanoimidazo[1,2-b]pyridazin-8-yl)(4-methoxybenzyl)amino)-N-(2-(dimethylamino)ethyl)benzamide

HRID 889473Notes

Reaction equation

HRID 889473 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([N:13]([CH2:23][C:24]2[CH:29]=[CH:28][C:27]([O:30][CH3:31])=[CH:26][CH:25]=2)[C:14]2[CH:15]=[C:16]([CH:20]=[CH:21][CH:22]=2)[C:17]([OH:19])=O)[C:5]2[N:6]([C:8]([C:11]#[N:12])=[CH:9][N:10]=2)[N:7]=1.[CH3:32][N:33]([CH3:37])[CH2:34][CH2:35][NH2:36].F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1>CN(C=O)C>[Cl:1][C:2]1[CH:3]=[C:4]([N:13]([CH2:23][C:24]2[CH:29]=[CH:28][C:27]([O:30][CH3:31])=[CH:26][CH:25]=2)[C:14]2[CH:15]=[C:16]([CH:20]=[CH:21][CH:22]=2)[C:17]([NH:36][CH2:35][CH2:34][N:33]([CH3:37])[CH3:32])=[O:19])[C:5]2[N:6]([C:8]([C:11]#[N:12])=[CH:9][N:10]=2)[N:7]=1

Participants

5

Reactant 3

HCID 66053N,N-DimethylethylenediamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 593140063-((6-Chloro-3-cyanoimidazo[1,2-b]pyridazin-8-yl)(4-methoxybenzyl)amino)benzoic acid

Product 1

HCID 593137633-((6-Chloro-3-cyanoimidazo[1,2-b]pyridazin-8-yl)(4-methoxybenzyl)amino)-N-(2-(dimethylamino)ethyl)benzamideYield 93.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A stirred solution of 253C (55 mg, 0.127 mmol) in DMF (1.0 mL) was treated with N1,N1-dimethylethane-1,2-diamine (0.021 mL, 0.190 mmol), BOP (72.9 mg, 0.165 mmol) and TEA (0.035 mL, 0.254 mmol), and the reaction mixture was stirred at ambient temperature for 1 hour. The reaction mixture was concentrated, triturated with water, and the resulting white solid was collected by filtration to yield 253D (60.0 mg, 93.7% yield). HPLC: Rt=3.47 min. (PHENOMENEX® Luna C18 4.6×30 mm 3 u, A10-90% aqueous methanol containing 0.1% TFA in 2 min; 4 mL/min flow). MS (ES): m/z=504.1 [M+H]+.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customtriturated with water
  3. filtrationthe resulting white solid was collected by filtration

Sources & evidence

ORD record
ord-38a183524e164994b3ce93cf2c04b352
Source dataset
uspto-grants-2012_08
Patent number
US08252795B2

Reaction notes

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