HCID 178488374, compound → N-(7-hydroxy-2,3-dihydroimidazo[1,2-c]quinazolin-5-yl)pyridine-3-carboxamide

HRID 536223Notes

Reaction equation

HRID 536223 reaction equation
C[O:2][C:3]1[C:12]2[N:11]=[C:10]([NH:13][C:14](=[O:21])[C:15]3[CH:20]=[CH:19][CH:18]=[N:17][CH:16]=3)[N:9]3[CH2:22][CH2:23][N:24]=[C:8]3[C:7]=2[CH:6]=[CH:5][CH:4]=1>CN1C(=O)CCC1>[OH:2][C:3]1[C:12]2[N:11]=[C:10]([NH:13][C:14](=[O:21])[C:15]3[CH:20]=[CH:19][CH:18]=[N:17][CH:16]=3)[N:9]3[CH2:22][CH2:23][N:24]=[C:8]3[C:7]=2[CH:6]=[CH:5][CH:4]=1

Participants

3

Reactant 1

HCID 178488374HCID 178488374, compound

Product 1

HCID 178522515N-(7-hydroxy-2,3-dihydroimidazo[1,2-c]quinazolin-5-yl)pyridine-3-carboxamideYield 94%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

N-(7-Methoxy-2,3-dihydroimidazo[1,2-c]quinazolin-5-yl)nicotinamide (Step 5, 8.7 g, 27 mmol) in NMP (90 mL) was heated to 150° C. and Na2S (10.6 g, 135 mmol) was added portionwise. The reaction color briefly became blue-green, then changed back to yellow-brown. After stirring at this temperature for 1.5 h, the reaction was cooled to rt whereupon a yellow solid precipitated. The mixture was diluted with EtOAc (200 mL) and the solid collected by vacuum filtration. The solid was suspended in water (200 mL), the pH adjusted to ˜7 by the slow addition of aqueous 2N HCl and the mixture was stirred 2 h. The solid was collected via vacuum filtration and washed with water (50 mL) and finally with acetone (50 mL). High vacuum drying overnight gave the title compound (7.8 g, 93%): HPLC MS RT=0.34 min, MH+=308.2; 1H NMR (DMSO-d6+2 drops TFA-d) δ: 4.25-4.31 (2H, m), 4.57-4.64 (2H, m), 7.45-7.49 (2H, m), 7.69-7.72 (1H, m), 7.92 (1H, dd), 8.78 (1H, dt), 8.97 (1H, dd), 9.49 (1H, d).

Workup

  1. customprecipitated
  2. additionThe mixture was diluted with EtOAc (200 mL)
  3. filtrationthe solid collected by vacuum filtration
  4. additionthe pH adjusted to ˜7 by the slow addition of aqueous 2N HCl
  5. stirringthe mixture was stirred 2 h
  6. filtrationThe solid was collected via vacuum filtration
  7. washwashed with water (50 mL) and finally with acetone (50 mL)
  8. customHigh vacuum drying overnight

Sources & evidence

ORD record
ord-75d6e6c9b94440bfbbe16fade541b1c5
Source dataset
uspto-grants-2014_10
Patent number
US08859572B2

Reaction notes

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