HCID 86710427, compound → HCID 73214370, compound

HRID 1398447Notes

Reaction equation

HRID 1398447 reaction equation
COC1C=CC(C[N:8]2[C:17]3[CH:18]=[C:19]([O:22][CH2:23][C@@H:24]([NH:29]C(=O)OC(C)(C)C)[CH2:25][CH:26]([CH3:28])[CH3:27])[CH:20]=[CH:21][C:16]=3[C:15]3[C:10](=[C:11]([CH3:37])[N:12]=[CH:13][CH:14]=3)[C:9]2=[O:38])=CC=1>C(#N)C.C(OCC)(=O)C.O>[NH2:29][C@@H:24]([CH2:25][CH:26]([CH3:28])[CH3:27])[CH2:23][O:22][C:19]1[CH:20]=[CH:21][C:16]2[C:15]3[C:10](=[C:11]([CH3:37])[N:12]=[CH:13][CH:14]=3)[C:9](=[O:38])[NH:8][C:17]=2[CH:18]=1

Participants

5

Reactant 1

HCID 86710427HCID 86710427, compound

Product 1

HCID 73214370HCID 73214370, compoundYield 80.2%

Reagents, catalysts & solvents 3

HCID 962WaterSolvent2×HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of (S)-tert-butyl (1-((6-(4-methoxybenzyl)-4-methyl-5-oxo-5,6-dihydrobenzo[c][2,7]naphthyridin-8-yl)oxy)-4-methylpentan-2-yl)carbamate (500 mg, 0.192 mmol) (prepared as described in Example 49), in acetonitrile (5 mL) and water (5 mL) was added ceric ammonium nitrate (527 mg, 0.962 mmol). The reaction mixture was stirred for 5 h at room temperature. The reaction mixture was diluted with ethyl acetate (5 mL) and water (5 mL). The organic layer was separated, dried with sodium sulfate and concentrated under reduced pressure. The residue was purified by silica gel chromatography (1:1 ethyl acetate:hexane) to afford (S)-8-(2-amino-4-methylpentyloxy)-4-methylbenzo[c][2,7]naphthyridin-5(6H)-one (100 mg, 0.154 mmol, 80% yield) as an off-white solid. LC/MS (ESI) m/e 326.2 [(M+H)+, calcd for C19H24N3O2 326.2] LC/MS retention time (method C): tR=1.56 min. HPLC retention time (method A): tR=6.98 min; HPLC retention time (method B): tR=6.96 min. 1H NMR (400 MHz, CD3OD) δ ppm 6.32 (m, 1H), 8.44 (m, 2H), 7.13 (m, 1H), 6.94 (d, J=2.4 Hz, 1H), 4.4 (m, 1H), 4.3 (m, 1H), 3.75 (m, 1H), 3.2 (s, 3H), 1.75 (m, 3H), 1.10 (m, 6H).

Workup

  1. customThe organic layer was separated
  2. dry with materialdried with sodium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by silica gel chromatography (1:1 ethyl acetate:hexane)

Sources & evidence

ORD record
ord-92893fc0c8344d28a07f19835854a2cf
Source dataset
uspto-grants-2014_12
Patent number
US08901305B2

Reaction notes

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