HCID 16749548, compound → HCID 16749115, compound

HRID 901162Notes

Reaction equation

HRID 901162 reaction equation
C([O:8][C:9]1[C:29]([O:30][CH3:31])=[CH:28][C:12]([CH2:13][N:14]([N:23]2[CH:27]=[N:26][N:25]=[CH:24]2)[C:15]2[CH:22]=[CH:21][C:18]([C:19]#[N:20])=[CH:17][CH:16]=2)=[CH:11][C:10]=1[Cl:32])C1C=CC=CC=1>[Pd].C(O)C.C1COCC1>[Cl:32][C:10]1[CH:11]=[C:12]([CH:28]=[C:29]([O:30][CH3:31])[C:9]=1[OH:8])[CH2:13][N:14]([N:23]1[CH:27]=[N:26][N:25]=[CH:24]1)[C:15]1[CH:16]=[CH:17][C:18]([C:19]#[N:20])=[CH:21][CH:22]=1

Participants

5

Reactant 1

HCID 16749548HCID 16749548, compound

Product 1

HCID 16749115HCID 16749115, compound

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

Palladium on charcoal (100 mg, 5% Pd) was added to a solution of 4-[(4-benzyloxy-3-chloro-5-methoxy-benzyl)-[1,2,4]triazol-4-yl-amino]-benzonitrile (CAB02177, 1.34 g, 3.0 mmol) in ethanol (60 mL) and THF (40 mL). The mixture was stirred under hydrogen atmosphere (balloon) for 24 h (TLC monitored), then filtered through celite and concentrated under reduced pressure. The residue was dried under high vacuum. Yield: 1.06 g (99%), white powder. 1H-NMR (400 MHz, d6-DMSO) δ=3.77 (s, 3H, —OCH3), 4.92 (s, 2H), 6.79 (d, J=9.0 Hz, 2H), 6.81 (d, J=1.8 Hz, 1H), 6.85 (d, J=1.8 Hz, 1H), 7.77 (d, J=9.0 Hz, 2H), 8.79 (s, 2H), 9.49 (s, 1H, —OH). LRMS (FAB+): 356.0 (100, [M+H]+). HRMS (FAB+): 356.09234 C17H15N15O2Cl requires 356.091428.

Workup

  1. filtrationfiltered through celite and
  2. concentrationconcentrated under reduced pressure
  3. customThe residue was dried under high vacuum

Sources & evidence

ORD record
ord-39bafbbd0336452388bd5c9a1fe57dd9
Source dataset
uspto-grants-2008_04
Patent number
US07361677B2

Reaction notes

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