Diisopropylethylamine → HCID 86729703, compound

HRID 1507650Notes

Reaction equation

HRID 1507650 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.[Br:23][C:24]1[CH:25]=[C:26]([C:36](O)=[O:37])[N:27]([C:29]2[CH:34]=[CH:33][C:32]([F:35])=[CH:31][CH:30]=2)[N:28]=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>[Br:23][C:24]1[CH:25]=[C:26]([C:36]([NH:2][C:3]2[CH:4]=[CH:5][C:6]([CH3:22])=[C:7]([NH:9][C:10]3[CH:11]=[C:12]4[C:17](=[CH:18][CH:19]=3)[N:16]=[CH:15][N:14]([CH3:20])[C:13]4=[O:21])[CH:8]=2)=[O:37])[N:27]([C:29]2[CH:34]=[CH:33][C:32]([F:35])=[CH:31][CH:30]=2)[N:28]=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 50990511HCID 50990511, compoundHCID 86729702HCID 86729702, compound

Product 1

HCID 86729703HCID 86729703, compoundYield 68.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

6-(5-Amino-2-methyl-phenylamino)-3-methyl-3H-quinazolin-4-one HCl salt (30 mg, 0.08 mmol) was dissolved in DMF (5 mL) with 5-bromo-2-(4-fluoro-phenyl)-2H-pyrazole-3-carboxylic acid (45 mg, 0.16 mmol) at RT. HATU (60 mg, 0.16 mmol) was added, followed by DIEA (0.14 mL, 0.8 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. 30 mg of title compound was obtained after lyophilization of pure fractions. LC-MS [M+H] 549.0.

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-ee0fa220abb441759ee8b7d9b50075bb
Source dataset
uspto-grants-2015_12
Patent number
US09221805B2

Reaction notes

Loading…