Sodium Hydroxide → HCID 11604420, compound

HRID 1373968Notes

Reaction equation

HRID 1373968 reaction equation
[NH2:1][C:2]1[C:11]2[N:12]=[C:13]([CH2:28][O:29][CH2:30][CH3:31])[N:14]([NH:15][CH2:16][CH2:17][CH2:18][NH:19][C:20]([N:22]3[CH2:27][CH2:26][O:25][CH2:24][CH2:23]3)=[O:21])[C:10]=2[C:9]2[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=2[N:3]=1.[OH-].[Na+]>C(O)(C(F)(F)F)=O.C(Cl)(Cl)Cl.O.[Pt](=O)=O>[NH2:1][C:2]1[C:11]2[N:12]=[C:13]([CH2:28][O:29][CH2:30][CH3:31])[N:14]([NH:15][CH2:16][CH2:17][CH2:18][NH:19][C:20]([N:22]3[CH2:27][CH2:26][O:25][CH2:24][CH2:23]3)=[O:21])[C:10]=2[C:9]2[CH2:8][CH2:7][CH2:6][CH2:5][C:4]=2[N:3]=1

Participants

7

Reactant 2

HCID 14798Sodium HydroxideHCID 10025549HCID 10025549, compound

Product 1

HCID 11604420HCID 11604420, compoundYield 41.2%

Reagents, catalysts & solvents 4

HCID 345198Adams' catalystCatalystHCID 962WaterSolventHCID 6212ChloroformSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of N-(3-{[4-amino-2-(ethoxymethyl)-1 H-imidazo[4,5-c]quinolin-1-yl]amino}propyl)morpholine-4-carboxamide (0.120 g, 0.281 mmol) in 12 mL of TFA was treated with platinum (IV) oxide (0.064 g, 0.28 mmol). The mixture was placed under an atmosphere of hydrogen (3.8×105 Pa) and shaken at ambient temperature. After 17 h, the reaction mixture was diluted with 15 mL of 4:1 CHCl3:MeOH and then filtered through a pad of CELITE filter agent and rinsed through with portions of 4:1 CHCl3:MeOH (1% TFA). The clear colorless filtrate was concentrated under reduced pressure to yield a white solid. The material was suspended in 15 mL of H2O and treated with 10% NaOH solution until the pH of the liquid was 13. A white solid was collected by vacuum filtration. The solid was purified by chromatography (SiO2, 25–30% (80:18:2 CHCl3:MeOH:NH4OH) in CHCl3) to yield a white foam. The foam was triturated with Et2O and filtered to yield N-(3-{[4-amino-2-(ethoxymethyl)-6,7,8,9-tetrahydro-1H-imidazo[4,5-c]quinolin-1-yl]amino}propyl)morpholine-4-carboxamide (0.050 g) as a white solid. mp 152–154° C.; 1H NMR (300 MHz, DMSO-d6) δ 6.52 (t, J=5.4 Hz, 1H), 6.31 (t, J=5.9 Hz, 1H), 5.83 (s, 2H), 4.61 (s, 2H), 3.58–3.50 (m, 6H), 3.24–3.21 (m, 4H), 3.12 (q, J=6.7 Hz, 2H), 3.06–3.00 (m, 4H), 2.67–2.64 (m, 2H), 1.78–1.72 (m, 4H), 1.66–1.61 (m, 2H), 1.14 (t, J=7.0 Hz, 3H); 13C NMR (75 MHz, DMSO-d6) δ 157.6, 149.4, 148.9, 146.5, 137.1, 105.0, 65.8, 65.2, 62.9, 51.3, 43.7, 37.8, 32.0, 28.1, 22.8, 22.5, 22.0, 14.9; MS (APCI) m/z 432 (M+H)+; Anal. Calcd for C21H33N7O3•5H2O: C, 57.25; H, 7.78; N, 22.26; Found: C, 57.30; H, 7.82; N, 22.29.

Workup

  1. filtrationMeOH and then filtered through a pad of CELITE
  2. filtrationfilter agent
  3. washrinsed through with portions of 4:1 CHCl3
  4. concentrationThe clear colorless filtrate was concentrated under reduced pressure
  5. customto yield a white solid
  6. filtrationA white solid was collected by vacuum filtration
  7. customThe solid was purified by chromatography (SiO2, 25–30% (80:18:2 CHCl3:MeOH:NH4OH) in CHCl3)
  8. customto yield a white foam
  9. customThe foam was triturated with Et2O
  10. filtrationfiltered

Sources & evidence

ORD record
ord-ab93d898ee7a45e9a4a1b0667277e27b
Source dataset
uspto-grants-2007_01
Patent number
US07163947B2

Reaction notes

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