Diisopropylethylamine → HCID 178426581, compound

HRID 1507653Notes

Reaction equation

HRID 1507653 reaction equation
OC(C(F)(F)F)=O.[N:8]1[CH:9]=[C:10]([C:17]#[C:18][C:19]2[CH:20]=[C:21]([NH2:26])[CH:22]=[CH:23][C:24]=2[CH3:25])[N:11]2[C:16]=1[CH:15]=[CH:14][CH:13]=[N:12]2.[F:27][C:28]1[CH:33]=[CH:32][C:31]([C:34]2[NH:38][C:37]([S:39]([CH3:42])(=[O:41])=[O:40])=[N:36][C:35]=2[C:43](O)=[O:44])=[CH:30][CH:29]=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C>CN(C=O)C.O>[F:27][C:28]1[CH:29]=[CH:30][C:31]([C:34]2[NH:38][C:37]([S:39]([CH3:42])(=[O:41])=[O:40])=[N:36][C:35]=2[C:43]([NH:26][C:21]2[CH:22]=[CH:23][C:24]([CH3:25])=[C:19]([C:18]#[C:17][C:10]3[N:11]4[N:12]=[CH:13][CH:14]=[CH:15][C:16]4=[N:8][CH:9]=3)[CH:20]=2)=[O:44])=[CH:32][CH:33]=1

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 86729706HCID 86729706, compoundHCID 178504849HCID 178504849, compound

Product 1

HCID 178426581HCID 178426581, compoundYield 49.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

3-Imidazo[1,2-b]pyridazin-3-ylethynyl-4-methyl-phenylamine TFA salt (200 mg, 0.55 mmol) was dissolved in DMF (5 mL) with 5-(4-fluoro-phenyl)-2-methanesulfonyl-1H-imidazole-4-carboxylic acid (204 mg, 0.72 mmol) at RT. HATU (300 mg, 0.79 mmol) was added, followed by DIEA (0.6 mL, 3.44 mmol). The mixture was stirred for 20 h. Water (10 mL) was added and the mixture was extracted with EtOAc (30 mL). The organic layer was concentrated and the residue was dissolved in minimum amount of DMSO and purified by prep HPLC. 140 mg of title compound was obtained after lyophilization of pure fractions. LC-MS [M+H] 515.2.

Workup

  1. extractionthe mixture was extracted with EtOAc (30 mL)
  2. concentrationThe organic layer was concentrated
  3. dissolutionthe residue was dissolved in minimum amount of DMSO
  4. custompurified by prep HPLC

Sources & evidence

ORD record
ord-f12e4464952245d3bc8bd06bf1d5f11e
Source dataset
uspto-grants-2015_12
Patent number
US09221805B2

Reaction notes

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