Diisopropylethylamine → HCID 86729701, compound

HRID 1507649Notes

Reaction equation

HRID 1507649 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]([C:30]2[O:34][C:33]([S:35]([CH3:38])(=[O:37])=[O:36])=[N:32][C:31]=2[C:39](O)=[O:40])=[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:25]=[CH:26][C:27]([C:30]2[O:34][C:33]([S:35]([CH3:38])(=[O:37])=[O:36])=[N:32][C:31]=2[C:39]([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:40])=[CH:28][CH:29]=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 71255699HCID 71255699, compoundHCID 86729702HCID 86729702, compound

Product 1

HCID 86729701HCID 86729701, compoundYield 53.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

6-(5-amino-2-methyl-phenylamino)-3-methyl-3H-quinazolin-4-one HCl salt (110 mg, 0.28 mmol) was dissolved in DMF (5 mL) with 5-(4-fluoro-phenyl)-2-methanesulfonyl-oxazole-4-carboxylic acid (142 mg, 0.5 mmol) at RT. HATU (150 mg, 0.39 mmol) was added, followed by DIEA (0.5 mL, 2.87 mmol). The mixture was stirred for 20 h. Water (20 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. 82 mg of title compound was obtained after lyophilization of pure fractions. LC-MS [M+H] 548.1.

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-4a328f9501f641be80ed2516e285e1b1
Source dataset
uspto-grants-2015_12
Patent number
US09221805B2

Reaction notes

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