Diisopropylethylamine → HCID 136636244, compound

HRID 923630Notes

Reaction equation

HRID 923630 reaction equation
[C:1]([C:3]1[CH:4]=[CH:5][C:6](F)=[C:7]([CH:11]=1)[C:8]([OH:10])=O)#[N:2].O.Cl.[C:15](=[NH:23])([NH2:22])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.CCN(C(C)C)C(C)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C.O>[O:10]=[C:8]1[C:7]2[C:6](=[CH:5][CH:4]=[C:3]([C:1]#[N:2])[CH:11]=2)[N:22]=[C:15]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[NH:23]1

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 27784625-Cyano-2-fluorobenzoic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 16219042Benzamidine HCl hydrate

Product 1

HCID 136636244HCID 136636244, compoundYield 55%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A stirring solution of 5-cyano-2-fluorobenzoic acid (2.02 g, 12.2 mmol) and benzimidamide hydrochloride monohydrate (2.14 g, 12.2 mmol) in DMF (15 mL) was treated with DIEA (5.34 mL, 30.6 mmol) and HATU (4.65 g, 12.2 mmol). The reaction mixture was stirred at room temperature for 30 min then heated at 100° C. for 18 h. The reaction mixture was cooled to room temperature and water (200 mL) was added. A precipitate formed which was isolated by filtration and dried under vacuum to afford 1.66 g (54%) of 4-oxo-2-phenyl-3,4-dihydroquinazoline-6-carbonitrile INT-87 as a light powdery white solid. LCMS-ESI (m/z) calculated for C15H9N3O: 247; found 248 [M+H]+, tR=1.70 min (Method 10).

Workup

  1. temperaturethen heated at 100° C. for 18 h
  2. temperatureThe reaction mixture was cooled to room temperature
  3. customA precipitate formed which
  4. customwas isolated by filtration
  5. customdried under vacuum

Sources & evidence

ORD record
ord-18a6247045dc40418f65e8217d218ef7
Source dataset
uspto-grants-2016_03
Patent number
US09278910B2

Reaction notes

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