Acetonitrile → HCID 58574738, compound

HRID 1619304Notes

Reaction equation

HRID 1619304 reaction equation
[NH:1]1[CH2:4][CH:3]([C:5]2[N:14]([CH3:15])[C:13](=[O:16])[C:12]3[C:7](=[CH:8][C:9]([C:17]#[C:18][C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][N:20]=4)=[CH:10][CH:11]=3)[N:6]=2)[CH2:2]1.Br[CH2:26][C:27]#[N:28].C([O-])([O-])=O.[K+].[K+].CC#N>O>[CH3:15][N:14]1[C:13](=[O:16])[C:12]2[C:7](=[CH:8][C:9]([C:17]#[C:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][N:20]=3)=[CH:10][CH:11]=2)[N:6]=[C:5]1[CH:3]1[CH2:2][N:1]([CH2:26][C:27]#[N:28])[CH2:4]1

Participants

6

Reactant 4

HCID 6342AcetonitrileHCID 11430Potassium CarbonateHCID 11534BromoacetonitrileHCID 58574715HCID 58574715, compound

Product 1

HCID 58574738HCID 58574738, compoundYield 44.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The mixture of 2-(azetidin-3-yl)-3-methyl-7-(pyridin-2-ylethynyl)quinazolin-4(3H)-one (100 mg, 0.316 mmol), 2-bromoacetonitrile (0.024 mL, 0.348 mmol), K2CO3 (87 mg, 0.632 mmol) and CH3CN (5 mL) was stirred at room temperature for 3 h, then diluted with water (10 mL). The mixture was then extracted with ethyl acetate (3×10 mL). The combined organic layers were dried over Na2SO4, filtered, and evaporated to give the crude product, which was purified by column chromatography to give 50 mg of the desired product. MS (ESI): 356 (MH+); 1H NMR (300 MHz, CDCl3) δ 8.68-8.67 (d, J=4.4 Hz, 1H), 8.27-8.24 (d, J=8.2 Hz, 1H), 7.95 (s, 1H), 7.77-7.71 (m, 1H), 7.67-7.64 (dd, J=8.2, 1.5 Hz, 1H), 7.60-7.58 (d, J=7.8 Hz, 1H), 7.33-7.28 (m, 1H), 3.92-3.89 (m, 5H), 3.56 (s, 2H), 3.50 (s, 3H).

Workup

  1. extractionThe mixture was then extracted with ethyl acetate (3×10 mL)
  2. dry with materialThe combined organic layers were dried over Na2SO4
  3. filtrationfiltered
  4. customevaporated
  5. customto give the crude product, which
  6. customwas purified by column chromatography

Sources & evidence

ORD record
ord-244b13ab17c148ab80130ed28471dbdb
Source dataset
uspto-grants-2014_07
Patent number
US08772301B2

Reaction notes

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