Trifluoroacetic acid → HCID 9841718, compound

HRID 1383821Notes

Reaction equation

HRID 1383821 reaction equation
FC(F)(F)C(O)=O.C(OC([N:15]1[CH2:24][CH2:23][C:22]2[C:21]3=[N:25][N:26]=[C:27]([C:28]4[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=4)[N:20]3[N:19]=[C:18]([O:34][CH2:35][C:36]3[CH:41]=[CH:40][CH:39]=[CH:38][N:37]=3)[C:17]=2[CH2:16]1)=O)(C)(C)C>ClCCl>[C:28]1([C:27]2[N:20]3[N:19]=[C:18]([O:34][CH2:35][C:36]4[CH:41]=[CH:40][CH:39]=[CH:38][N:37]=4)[C:17]4[CH2:16][NH:15][CH2:24][CH2:23][C:22]=4[C:21]3=[N:25][N:26]=2)[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 53676051HCID 53676051, compound

Product 1

HCID 9841718HCID 9841718, compoundYield 96.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic acid (3 ml) was added to a solution of 3-phenyl-5-(pyridin-2-ylmethoxy)-8,9-dihydro-6H-1,2,3a,4,7-pentaazacyclopenta[α]-naphthalene-7-carboxylic acid tert-butyl ester (217 mg, 0.47 mmol) in dry dichloromethane (3 ml) at 0° C. under nitrogen. After 1 hour the volatiles were removed in vacuo and the residue was partitioned between dichloromethane and saturated aqueous potassium carbonate. The aqueous was further extracted with dichloromethane (×2). The combined extracts were dried (Na2SO4), filtered and evaporated. The residue was purified by chromatography on silica gel, eluting with dichloromethane/methanol/ammonia (60:8:1) to afford the title amine (162 mg, 96%) as a colourless solid, m.p.=157-159° C. 1H NMR (360 MHz, d6-DMSO) δ2.92-2.96 (2H, m), 3.07 (2H, t, J=5.8 Hz), 3.84 (2H, s), 5.56 (2H, s), 7.36 (1H, dd, J=6.7, 4.9 Hz), 7.52-7.60 (4H, m), 7.87 (1H, td, J=7.8, 1.7), 8.23 (2H, dd, J=6.3, 1.9 Hz), 8.62-8.64 (1H, m). MS (ES+) m/e 359 [MH]+. Anal. Found C, 64.93; H, 5.31; N, 22.30. C20H18N6O.0.75 H2O requires C, 64.59; H, 5.29; N, 22.60%.

Workup

  1. customAfter 1 hour the volatiles were removed in vacuo
  2. customthe residue was partitioned between dichloromethane and saturated aqueous potassium carbonate
  3. extractionThe aqueous was further extracted with dichloromethane (×2)
  4. dry with materialThe combined extracts were dried (Na2SO4)
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue was purified by chromatography on silica gel
  8. washeluting with dichloromethane/methanol/ammonia (60:8:1)

Sources & evidence

ORD record
ord-82b3196103db424bb4d2f19ac1ea9d7a
Source dataset
uspto-grants-2001_07
Patent number
US06255305B1

Reaction notes

Loading…