Benzaldehyde → HCID 69119399, compound

HRID 1375624Notes

Reaction equation

HRID 1375624 reaction equation
[CH3:1][N:2]([CH2:4][C:5]1[N:6]([C:10]2[CH:15]=[CH:14][C:13]([N:16]3[CH2:21][CH2:20][CH2:19][NH:18][C:17]3=[O:22])=[C:12]([F:23])[CH:11]=2)[CH:7]=[CH:8][N:9]=1)[CH3:3].[N:24]([O-])=O.[Na+].[CH:28](=O)[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1.[OH-].[Na+]>OS(O)(=O)=O.[Zn]>[CH:28](=[N:24][N:18]1[CH2:19][CH2:20][CH2:21][N:16]([C:13]2[CH:14]=[CH:15][C:10]([N:6]3[CH:7]=[CH:8][N:9]=[C:5]3[CH2:4][N:2]([CH3:1])[CH3:3])=[CH:11][C:12]=2[F:23])[C:17]1=[O:22])[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1

Participants

7

Reactant 4

HCID 240BenzaldehydeHCID 14798Sodium HydroxideHCID 23668193Sodium NitriteHCID 58787207HCID 58787207, compound

Product 1

HCID 69119399HCID 69119399, compound

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 1118Sulfuric AcidSolvent

Conditions

Temperature
0 °C

Procedure

Previously prepared 1-[4-(2-dimethylaminomethyl-imidazol-1-yl)-2-fluoro-phenyl]-tetrahydro-pyrimidin-2-one, (475.5 mg; 1.5 mmol) was dissolved in 10 mL of 10% H2SO4 solution. The mixture was then cooled to 0° C. and 103.5 mg, (1.5 mmol) of NaNO2 were added portionwise. After 3h at 0° C., 245.2 mg (3.75 mmol) of Zn dust were added in small portions. Bubbling occurred immediately. After the end of intense bubbling, the cooling bath was removed, and the mixture stirred 1 h at the room temperature. The mixture was filtered through Celite® 545 to remove suspensions. 143.3 mg (1.35 mmol) of benzaldehyde were then introduced, and the reaction mixture stirred for 2 h. The pH of the mixture was made neutral with NaOH prior to extractions with CH2Cl2. The organic phases were dried over MgSO4 and concentrated to yield 364.3 mg of the target material as a viscous oil. An analytically pure sample was obtained after purification on an IST Isolute Flash Cartridge (loading with CH2Cl2 and eluting with 5% MeOH/CH2Cl2). 1H NMR (400 MHz, CDCl3) δ 8.11 (s, 1H), 7.76 (m, 2H), 7.62 (dd, 1H), 7.49 (t, 1H), 7.3–7.4 (m, 4H), 7.11 (d, 2H), 3.89 (t, 2H), 3.73 (t, 2H), 3.42 (s, 2H), 2.41 (m, 2H), 2.3 (s, 6H), ppm. LC-MS (ESI) 421.1 [M+H]+, tR=3.207 min (Shimadzu Phenomenex S5 ODS 4.6×50 mm Luna flow rate 2.5 ml/mn; detection at 220 nM; Gradient elution 0% to 100% B over 8 min; (A=10% MeOH, 90% H2O, 0.2% H3PO4& B=90% MeOH, 10% H2O, 0.2% H3PO4). HRMS (ESI) m/z calcd for C23H26N6OF [M+H]+ 421.2152, found 421.2147.

Workup

  1. customBubbling
  2. customAfter the end of intense bubbling, the cooling bath was removed
  3. filtrationThe mixture was filtered through Celite® 545
  4. customto remove suspensions
  5. stirringthe reaction mixture stirred for 2 h
  6. extractionto extractions with CH2Cl2
  7. dry with materialThe organic phases were dried over MgSO4
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-3366502dcedb4360b423f5243c6ab04e
Source dataset
uspto-grants-2007_01
Patent number
US07169795B2

Reaction notes

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