Diisopropylethylamine → HCID 90337807, compound

HRID 1507652Notes

Reaction equation

HRID 1507652 reaction equation
Cl.[NH2:2][C:3]1[CH:4]=[CH:5][C:6]([CH3:22])=[C:7]([NH:9][C:10]2[CH:11]=[C:12]3[C:17](=[CH:18][CH:19]=2)[N:16]=[CH:15][N:14]([CH3:20])[C:13]3=[O:21])[CH:8]=1.[F:23][C:24]1[CH:29]=[CH:28][C:27]([N:30]2[C:34]([C:35](O)=[O:36])=[CH:33][C:32]([S:38]([CH3:41])(=[O:40])=[O:39])=[N:31]2)=[CH:26][CH:25]=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:23][C:24]1[CH:29]=[CH:28][C:27]([N:30]2[C:34]([C:35]([NH:2][C:3]3[CH:4]=[CH:5][C:6]([CH3:22])=[C:7]([NH:9][C:10]4[CH:11]=[C:12]5[C:17](=[CH:18][CH:19]=4)[N:16]=[CH:15][N:14]([CH3:20])[C:13]5=[O:21])[CH:8]=3)=[O:36])=[CH:33][C:32]([S:38]([CH3:41])(=[O:39])=[O:40])=[N:31]2)=[CH:26][CH:25]=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 86729698HCID 86729698, compoundHCID 86729702HCID 86729702, compound

Product 1

HCID 90337807HCID 90337807, compoundYield 20.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

6-(5-Amino-2-methyl-phenylamino)-3-methyl-3H-quinazolin-4-one HCl salt (138 mg, 0.49 mmol) was dissolved in DMF (2 mL) with 2-(4-fluoro-phenyl)-5-methanesulfonyl-2H-pyrazole-3-carboxylic acid (140 mg, 0.49 mmol) at RT. HATU (186 mg, 0.54 mmol) was added, followed by DIEA (0.21 mL, 1.2 mmol). The mixture was stirred for 20 h. Water (10 mL) was added and the mixture was extracted with EtOAc (20 mL). The organic layer was concentrated and the residue was dissolved in minimum amount of DMSO and purified by prep HPLC. 55 mg of title compound was obtained after lyophilization of pure fractions. LC-MS [M+H] 547.2.

Workup

  1. extractionthe mixture was extracted with EtOAc (20 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-980874280fa441329603b3f884f91ed5
Source dataset
uspto-grants-2015_12
Patent number
US09221805B2

Reaction notes

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