Diisopropylethylamine → HCID 178426580, compound

HRID 1507654Notes

Reaction equation

HRID 1507654 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.[CH3:27][N:28]([CH3:47])[CH2:29][CH2:30][S:31][C:32]1[NH:33][C:34]([C:40]2[CH:45]=[CH:44][C:43]([F:46])=[CH:42][CH:41]=2)=[C:35]([C:37](O)=[O:38])[N:36]=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>[CH3:27][N:28]([CH3:47])[CH2:29][CH2:30][S:31][C:32]1[NH:33][C:34]([C:40]2[CH:41]=[CH:42][C:43]([F:46])=[CH:44][CH:45]=2)=[C:35]([C:37]([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:38])[N:36]=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 178483976HCID 178483976, compound

Product 1

HCID 178426580HCID 178426580, compoundYield 80.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

3-Imidazo[1,2-b]pyridazin-3-ylethynyl-4-methyl-phenylamine TFA salt (450 mg, 1.24 mmol) was dissolved in DMF (10 mL) with 2-(2-Dimethylamino-ethylthio)-5-(4-fluoro-phenyl)-1H-imidazole-4-carboxylic acid (575 mg, 1.86 mmol) at RT. HATU (700 mg, 1.86 mmol) was added, followed by DIEA (1.3 mL, 7.44 mmol). The mixture was stirred for 20 h. Water (80 mL) was added and the mixture was extracted with EtOAc (300 mL). The organic layer was concentrated and the residue was dissolved in minimum amount of DMSO and purified by prep HPLC. 540 mg of title compound was obtained after lyophilization of pure fractions. LC-MS [M+H] 540.3.

Workup

  1. extractionthe mixture was extracted with EtOAc (300 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-688da6ebf8d444c5bf61c90f0d6b0203
Source dataset
uspto-grants-2015_12
Patent number
US09221805B2

Reaction notes

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