Trifluoroacetic acid → HCID 178493831, compound

HRID 339768Notes

Reaction equation

HRID 339768 reaction equation
C([O:8][C:9]1[CH:10]=[CH:11][C:12]2[C:13]3[N:14]([CH2:30][CH2:31][N:32]=3)[C:15]([NH:21][C:22](=[O:29])[C:23]3[CH:28]=[CH:27][CH:26]=[N:25][CH:24]=3)=[N:16][C:17]=2[C:18]=1[O:19][CH3:20])C1C=CC=CC=1.C(O)(C(F)(F)F)=O>CO>[OH:8][C:9]1[CH:10]=[CH:11][C:12]2[C:13]3[N:14]([CH2:30][CH2:31][N:32]=3)[C:15]([NH:21][C:22](=[O:29])[C:23]3[CH:28]=[CH:27][CH:26]=[N:25][CH:24]=3)=[N:16][C:17]=2[C:18]=1[O:19][CH3:20]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 178493819HCID 178493819, compound

Product 1

HCID 178493831HCID 178493831, compoundYield 113.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

N-[8-(Benzyloxy)-7-methoxy-2,3-dihydroimidazo[1,2-c]quinazolin-5-yl]nicotinamide (20 g, 45.1 mmol) was added portionwise over 1 h to a round bottom flask containing TFA (400 mL) precooled with an ice bath. The reaction mixture was heated to 60° C. and allowed to stir at this temperature for 17 h at which time it was cooled to room temperature. The reaction mixture was then concentrated under reduced pressure. The resulting residue was dissolved in CH2Cl2 and hexane and concentrated under reduced pressure. The material thus obtained was dissolved in MeOH and CH2Cl2 (250 mL, 1:1) and concentrated under reduced pressure. The resulting solids were dried overnight under vacuum with low heat to give N-(8-hydroxy-7-methoxy-2,3-dihydroimidazo[1,2-c]quinazolin-5-yl)nicotinamide (17.3 g, 66%): 1H NMR (DMSO-d6+2 drops TFA-d) δ: 13.41 (1H, s), 12.21 (1H, br s), 9.38 (1H, s), 8.78 (1H, d), 8.53 (1H, d), 7.85 (1H, d), 7.59 (1H, m), 7.17 (1H, d), 4.54 (2H, m), 4.21 (2H, m), 3.98 (3H, s); mass spectrum m/z 481 ((M+1)+).

Workup

  1. customprecooled with an ice bath
  2. temperaturewas cooled to room temperature
  3. concentrationThe reaction mixture was then concentrated under reduced pressure
  4. dissolutionThe resulting residue was dissolved in CH2Cl2
  5. concentrationhexane and concentrated under reduced pressure
  6. customThe material thus obtained
  7. concentrationCH2Cl2 (250 mL, 1:1) and concentrated under reduced pressure
  8. customThe resulting solids were dried overnight under vacuum
  9. temperaturewith low heat

Sources & evidence

ORD record
ord-09157085d659441296afeb5ec675274a
Source dataset
uspto-grants-2014_11
Patent number
US08895549B2

Reaction notes

Loading…