Trifluoroacetic acid → HCID 178493831, compound

HRID 536217Notes

Reaction equation

HRID 536217 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 (Step 1, 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 ambient. The reaction mixture was then concentrated under reduced pressure. The resulting residue was taken up in DCM and hexane and concentrated under reduced pressure. The material thus obtained was dissolved in MeOH and DCM (250 mL, 1:1) and concentrated under reduced pressure. The resulting solids were dried overnight under vacuum with low heat to give the title compound (17.3 g, 66%): HPLC MS RT=1.09 min, MH+=481.2; 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).

Workup

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

Sources & evidence

ORD record
ord-89761e275ca84a6d8a1322dbf77d4bd5
Source dataset
uspto-grants-2014_10
Patent number
US08859572B2

Reaction notes

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