4-{[3-(4-Benzyloxy-benzenesulfonyl)-propyl]-[1,2,4]triazol-4-yl-amino}-benzonitrile → HCID 21976888, compound

HRID 901182Notes

Reaction equation

HRID 901182 reaction equation
C([O:8][C:9]1[CH:14]=[CH:13][C:12]([S:15]([CH2:18][CH2:19][CH2:20][N:21]([N:30]2[CH:34]=[N:33][N:32]=[CH:31]2)[C:22]2[CH:29]=[CH:28][C:25]([C:26]#[N:27])=[CH:24][CH:23]=2)(=[O:17])=[O:16])=[CH:11][CH:10]=1)C1C=CC=CC=1>[Pd].C1COCC1.C(O)C>[OH:8][C:9]1[CH:14]=[CH:13][C:12]([S:15]([CH2:18][CH2:19][CH2:20][N:21]([N:30]2[CH:31]=[N:32][N:33]=[CH:34]2)[C:22]2[CH:29]=[CH:28][C:25]([C:26]#[N:27])=[CH:24][CH:23]=2)(=[O:17])=[O:16])=[CH:11][CH:10]=1

Participants

5

Reactant 1

HCID 219768744-{[3-(4-Benzyloxy-benzenesulfonyl)-propyl]-[1,2,4]triazol-4-yl-amino}-benzonitrile

Product 1

HCID 21976888HCID 21976888, compound

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

Palladium on charcoal (50 mg, 10% Pd) was added to a solution of 4-{[3-(4-Benzyloxy-benzenesulfonyl)-propyl]-[1,2,4]triazol-4-yl-amino}-benzonitrile (CAB02168, 118 mg, 0.25 mmol) in THF (10 mL) and ethanol (10 mL). The mixture was stirred under hydrogen atmosphere (balloon) for 18 h at room temperature. The reaction mixture was filtered through celite and the clear colourless filtrate was concentrated under reduced pressure. The residue was crystallised from acetone/water. Yield: 68 mg (71%) colourless crystals. 1H-NMR (400 MHz, d6-DMSO) δ=1.68-1.76 (m, 2H), 3.38 (t, J=7.6 Hz, 2H), 3.92 (t, J=7.2 Hz, 2H), 6.57 (d, J=9.0 Hz, 2H), 6.95 (d, J=9.0 Hz, 2H), 7.68 (d, J=9.0 Hz, 2H), 7.73 (d, J=9.0 Hz, 2H), 8.97 (s, 2H), 10.64 (s, 1H, —OH). LRMS (FAB+): 384.0 (100, [M+H]+). HRMS (FAB+): 384.11248 C18H18N5O3S requires 384.11304.

Workup

  1. filtrationThe reaction mixture was filtered through celite
  2. concentrationthe clear colourless filtrate was concentrated under reduced pressure
  3. customThe residue was crystallised from acetone/water

Sources & evidence

ORD record
ord-7a6828490e364df596a3b5cedde32f63
Source dataset
uspto-grants-2008_04
Patent number
US07361677B2

Reaction notes

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