Toluene → HCID 42643911, compound

HRID 1969107Notes

Reaction equation

HRID 1969107 reaction equation
[NH2:1][C:2]1[C:3]2[N:4]([CH:28]=[CH:29][N:30]=2)[N:5]=[C:6]([C:8]2[C:9]([CH3:27])=[C:10]([NH:14][C:15](=[O:26])[C:16]3[CH:21]=[CH:20][C:19]([C:22]([CH3:25])([CH3:24])[CH3:23])=[CH:18][CH:17]=3)[CH:11]=[CH:12][CH:13]=2)[CH:7]=1.[CH:31]([N:34]([CH:37](C)C)CC)(C)[CH3:32].C(Cl)(Cl)=[O:41].C1(C)C=CC=CC=1>ClCCl>[C:22]([C:19]1[CH:20]=[CH:21][C:16]([C:15]([NH:14][C:10]2[CH:11]=[CH:12][CH:13]=[C:8]([C:6]3[CH:7]=[C:2]([NH:1][C:37]([NH:34][CH2:31][CH3:32])=[O:41])[C:3]4[N:4]([CH:28]=[CH:29][N:30]=4)[N:5]=3)[C:9]=2[CH3:27])=[O:26])=[CH:17][CH:18]=1)([CH3:25])([CH3:24])[CH3:23]

Participants

6

Reactant 4

HCID 1140TolueneHCID 6371PhosgeneHCID 81531DiisopropylethylamineHCID 44199211HCID 44199211, compound

Product 1

HCID 42643911HCID 42643911, compoundYield 58%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of N-[3-(8-amino-imidazo[1,2-b]pyridazin-6-yl)-2-methyl-phenyl]-4-tert-butyl-benzamide (0.019 g, 0.047 mmol) and diisopropylethylamine (0.021 mL, 0.12 mmol) in 1 mL of dichloromethane at 0-5° C. was added a 20% phosgene in toluene solution (0.030 mL, 0.057 mmol) all at once. The cloudy yellow solution was stirred for 10 min., then ethylamine gas was bubbled in via a Pasteur pipette for 2 min. Silica gel (3 g) was added, and the mixture was concentrated to a pale yellow powder. Column chromatography (66%->100% EtOAc/hexanes) afforded 0.013 g (58%) of 4-tert-butyl-N-{3-[8-(3-ethyl-ureido)-imidazo[1,2-b]pyridazin-6-yl]-2-methyl-phenyl}-benzamide as a white solid.

Workup

  1. customethylamine gas was bubbled in via a Pasteur pipette for 2 min
  2. additionSilica gel (3 g) was added
  3. concentrationthe mixture was concentrated to a pale yellow powder

Sources & evidence

ORD record
ord-d7b6abf134c0474aa88af6875b72cb9e
Source dataset
uspto-grants-2013_04
Patent number
US08426441B2

Reaction notes

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