HCID 70978090, compound → HCID 70978092, compound

HRID 2281065Notes

Reaction equation

HRID 2281065 reaction equation
Br[C:2]1[C:10]2[N:9]=[N:8][N:7]([CH2:11][CH:12]3[CH2:14][CH2:13]3)[C:6]=2[CH:5]=[CH:4][C:3]=1[C:15]1[CH:29]=[CH:28][C:18]([CH2:19][N:20]2[CH2:24][C:23](=[O:25])[N:22]([CH3:26])[C:21]2=[O:27])=[CH:17][CH:16]=1>CO.[Pd]>[CH:12]1([CH2:11][N:7]2[C:6]3[CH:5]=[CH:4][C:3]([C:15]4[CH:29]=[CH:28][C:18]([CH2:19][N:20]5[CH2:24][C:23](=[O:25])[N:22]([CH3:26])[C:21]5=[O:27])=[CH:17][CH:16]=4)=[CH:2][C:10]=3[N:9]=[N:8]2)[CH2:14][CH2:13]1

Participants

4

Reactant 1

HCID 70978090HCID 70978090, compound

Product 1

HCID 70978092HCID 70978092, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

1-{4-[4-Bromo-1-(cyclopropylmethyl)-1H-benzotriazol-5-yl]benzyl}-3-methylimidazolidine-2,4-dione (Example 10, 20 mg, 0.044 mmol) was dissolved in methanol (7 mL) and sparged under nitrogen. The vessel was charged with Pd/C (4.7 mg, 1 equiv), sparged under an atmosphere of hydrogen (1 atm) and vigorously stirred for 2 hours. The mixture was sparged under and atmosphere of nitrogen, filtered through a pad of Celite and the pad was washed with methanol (20 mL). The mixture was concentrated in vacuo and the residue was purified by preparative reverse phase HPLC (95:5 to 5:95; water containing 0.1% trifluoroacetic acid:acetonitrile containing 0.1% trifluoroacetic acid), providing the titled compound: 1H-NMR (400 MHz, d6-DMSO) δ 8.29 (1H, s), 8.02 (1H, d, J=9.2 Hz), 7.78 (1H, dd, J=8.7, 1.4 Hz), 7.78 (2H, d, J=8.3 Hz), 7.42 (2H, d, J=8.1 Hz), 4.64 (2H, d, J=7.3 Hz), 4.56 (2H, s), 3.93 (2H, s), 2.90 (3H, s), 1.43-1.35 (1H, m), 0.59-0.55 (2H, m), 0.51-0.48 (2H, m) ppm; high resolution mass spectrometry (ES+) m/z 376.1763 [(M+H)+; calculated for C21H22N5O2: 376.1768].

Workup

  1. customsparged under nitrogen
  2. customsparged under an atmosphere of hydrogen (1 atm)
  3. customThe mixture was sparged under and atmosphere of nitrogen
  4. filtrationfiltered through a pad of Celite
  5. washthe pad was washed with methanol (20 mL)
  6. concentrationThe mixture was concentrated in vacuo
  7. customthe residue was purified by preparative reverse phase HPLC (95:5 to 5:95; water containing 0.1% trifluoroacetic acid:acetonitrile containing 0.1% trifluoroacetic acid)

Sources & evidence

ORD record
ord-0818a787c93c45538a2f22d4bd92f85b
Source dataset
uspto-grants-2015_09
Patent number
US09139576B2

Reaction notes

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