HCID 71062764, compound → Tert-butyl 3-(2-{[(1S,2S)-2-(5-methoxypyridin-2-yl)cyclopropyl]methoxy}-1,5-naphthyridin-3-yl)piperidine-1-carboxylate

HRID 872064Notes

Reaction equation

HRID 872064 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([C@H:9]2[CH2:11][C@@H:10]2[CH2:12][O:13][C:14]2[C:23]([C:24]3[CH2:29][N:28]([C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])[CH2:27][CH2:26][CH:25]=3)=[CH:22][C:21]3[C:16](=[CH:17][CH:18]=[CH:19][N:20]=3)[N:15]=2)=[N:7][CH:8]=1>C(O)C.[Pd]>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([C@H:9]2[CH2:11][C@@H:10]2[CH2:12][O:13][C:14]2[C:23]([CH:24]3[CH2:25][CH2:26][CH2:27][N:28]([C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])[CH2:29]3)=[CH:22][C:21]3[C:16](=[CH:17][CH:18]=[CH:19][N:20]=3)[N:15]=2)=[N:7][CH:8]=1

Participants

4

Reactant 1

HCID 71062764HCID 71062764, compound

Product 1

HCID 71062617Tert-butyl 3-(2-{[(1S,2S)-2-(5-methoxypyridin-2-yl)cyclopropyl]methoxy}-1,5-naphthyridin-3-yl)piperidine-1-carboxylate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To tert-butyl 5-(2-{[(1S,2S)-2-(5-methoxypyridin-2-yl)cyclopropyl]methoxy}-1,5-naphthyridin-3-yl)-3,6-dihydropyridine-1(2H)-carboxylate (RR1) (50 mg, 0.10 mmol) in ethanol (2 mL) was carefully added 10% palladium on carbon (10.6 mg, 0.01 mmol) under N2. The reaction mixture was evacuated and backfilled three times with hydrogen via balloon and then stirred overnight at room temperature. Upon completion, the mixture was filtered through celite washing with methanol and concentrated in vacuo to afford the title compound. 1H NMR (500 MHz, DMSO): δ 8.77 (1 H, d, J=4.5 Hz), 8.12 (3 H, d, J=9.4 Hz), 7.64 (1 H, m), 7.24 (2 H, s), 4.53 (m, 2 H), 4.26 (m, 2 H), 3.77 (s, 3 H), 3.49-3.40 (m, 3 H), 2.27 (s, 2 H), 2.24-2.19 (m, 1 H), 1.99 (m, 1 H), 1.80 (s, 1 H), 1.41 (s, 9 H), 1.23-1.15 (m, 2 H), 1.08 (dt, J=8.7, 4.6 Hz, 1 H); HRMS m/z (M+H) 491.2654 found, 491.2653 required.

Workup

  1. customThe reaction mixture was evacuated
  2. filtrationUpon completion, the mixture was filtered
  3. washthrough celite washing with methanol
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-2dddc90fe4fd49cf9ed02fbcef8752ce
Source dataset
uspto-grants-2015_03
Patent number
US08975261B2

Reaction notes

Loading…