HCID 68862586, compound → HCID 68863638, compound

HRID 2099130Notes

Reaction equation

HRID 2099130 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][C:10]#[C:11][C:12]1[CH:13]=[C:14]2[C:19]3=[C:20]([CH2:22][CH2:23][CH2:24][N:18]3[CH:17]=[C:16]([C:25]([O:27][CH2:28][CH3:29])=[O:26])[C:15]2=[O:30])[CH:21]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>ClCCl>[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][CH2:11][C:12]1[CH:13]=[C:14]2[C:19]3=[C:20]([CH2:22][CH2:23][CH2:24][N:18]3[CH:17]=[C:16]([C:25]([O:27][CH2:28][CH3:29])=[O:26])[C:15]2=[O:30])[CH:21]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

3

Reactant 1

HCID 68862586HCID 68862586, compound

Product 1

HCID 68863638HCID 68863638, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Ethyl 9-(3-tert-butoxycarbonylamino-prop-1-ynyl)-1-oxo-6,7-dihydro-1H,5H-pyrido[3,2,1-ij]quinoline-2-carboxylate (318 mg, 0.77 mmol) was dissolved in dichloromethane (50 mL), treated with 10% palladiun on carbon (200 mg) and hydrogenated at room temperature and atmospheric pressure overnight. The reaction mixture was filtered and concentrated to provide a brown oil which was purified by chromatography on silica gel eluting with 0-1% (9:1 MeOH/20 M NH3) in dichloromethane to yield the title compound as a brown oil. ESMS m/z 415 (MH+). 1H NMR (CDCl3) δ 8.34 (s, 1H), 8.11 (bs, 1H), 7.25 (bs, 1H), 4.60 (m, 1H), 4.37 (q, 2H), 4.17 (t, 2H), 3.13 (q, 2H), 3.02 (t, 2H), 2.71 (t,2H), 2.20 (tt, 2H), 1.85 (tt, 2H), 1.44 (s, 9H), 1.40 (t, 3H).

Workup

  1. additiontreated with 10% palladiun on carbon (200 mg) and hydrogenated at room temperature
  2. customatmospheric pressure overnight
  3. filtrationThe reaction mixture was filtered
  4. concentrationconcentrated
  5. customto provide a brown oil which
  6. customwas purified by chromatography on silica gel eluting with 0-1% (9:1 MeOH/20 M NH3) in dichloromethane

Sources & evidence

ORD record
ord-71a9d9ae18f24ca7bd5aa628e0dd7d8d
Source dataset
uspto-grants-2009_08
Patent number
US07569550B2

Reaction notes

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