Water → HCID 11689619, compound

HRID 1373974Notes

Reaction equation

HRID 1373974 reaction equation
[NH2:1][C:2]1[C:11]2[N:12]=[C:13]([CH2:25][O:26][CH2:27][CH3:28])[N:14]([NH:15][CH2:16][CH2:17][CH2:18][NH:19][C:20](=[O:24])[CH:21]([CH3:23])[CH3:22])[C:10]=2[C:9]2[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=2[N:3]=1.O.[OH-].[Na+]>C(O)(C(F)(F)F)=O.[Pt](=O)=O>[NH2:1][C:2]1[C:11]2[N:12]=[C:13]([CH2:25][O:26][CH2:27][CH3:28])[N:14]([NH:15][CH2:16][CH2:17][CH2:18][NH:19][C:20](=[O:24])[CH:21]([CH3:23])[CH3:22])[C:10]=2[C:9]2[CH2:8][CH2:7][CH2:6][CH2:5][C:4]=2[N:3]=1

Participants

6

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 11696679HCID 11696679, compound

Product 1

HCID 11689619HCID 11689619, compoundYield 52.1%

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of N-(3-{[4-amino-2-(ethoxymethyl)-1H-imidazo[4,5-c]quinolin-1-yl]amino}propyl)-2-methylpropanamide (0.450 g, 1.17 mmol) in 25 mL of TFA was treated with platinum (IV) oxide (0.266 g, 1.17 mmol). The reaction mixture was shaken under an atmosphere of hydrogen (3.8×105 Pa) at ambient temperature. After 17 h, the reaction mixture was filtered through a pad of CELITE filter agent and rinsed with portions of 4:1 CHCl3:MeOH (1% TFA). The filtrate was concentrated under reduced pressure to yield a white oil. The oil was suspended in a minimum amount of H2O and treated with 50% NaOH solution until the pH was 13. A white solid precipitated and was triturated in the basic H2O for 1 h and then filtered to yield a sticky white solid. The solid was then triturated with Et2O for 2 h, filtered and dried to yield N-(3-{[4-amino-2-(ethoxymethyl)-6,7,8,9-tetrahydro-1H-imidazo[4,5-c]quinolin-1-yl]amino}propyl)-2-methylpropanamide (0.237 g) as a white solid. mp 163–165° C.; 1H NMR (500 MHz, DMSO-d6) δ 7.69 (t, J=5.5 Hz, 1H), 6.31 (t, J=5.9 Hz, 1H), 5.80 (s, 2H), 4.61 (s, 2H), 3.55 (q, J=7.0 Hz, 2H), 3.15–3.11 (m, 2H), 3.04–3.00 (m, 4H), 2.66 (t, J=5.7 Hz, 2H), 2.31 (h, J=6.8 Hz, 1H), 1.81–1.69 (m, 4H), 1.62 (p, J=7.1 Hz, 2H), 1.14 (t, J=7.0 Hz, 3H), 0.98 (d, J=6.9 Hz, 6H); 13C NMR (75 MHz, DMSO-d6) δ 176.3, 149.9, 149.3, 147.0, 137.6, 122.7, 105.4, 65.7, 63.3, 51.7, 36.6, 34.4, 32.5, 28.0, 23.3, 23.0, 22.4, 19.9, 15.3; MS (ESI) m/z 389 (M+H)+; Anal. Calcd for C20H32N6O2: C, 61.83; H, 8.30; N, 21.63; Found: C, 61.63; H, 8.23; N, 21.55.

Workup

  1. filtrationthe reaction mixture was filtered through a pad of CELITE
  2. filtrationfilter agent
  3. washrinsed with portions of 4:1 CHCl3
  4. concentrationThe filtrate was concentrated under reduced pressure
  5. customto yield a white oil
  6. customA white solid precipitated
  7. customwas triturated in the basic H2O for 1 h
  8. filtrationfiltered
  9. customto yield a sticky white solid
  10. customThe solid was then triturated with Et2O for 2 h
  11. filtrationfiltered
  12. customdried

Sources & evidence

ORD record
ord-7890109a9b20485d9d4ab77f7e22e8a4
Source dataset
uspto-grants-2007_01
Patent number
US07163947B2

Reaction notes

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