HCID 59529771, compound → HCID 59529781, compound

HRID 1952339Notes

Reaction equation

HRID 1952339 reaction equation
[N:1]([CH2:4][C:5]1[C:13]2[C:8](=[N:9][C:10]([F:14])=[CH:11][CH:12]=2)[N:7]([CH:15]2[CH2:20][CH2:19][CH2:18][CH2:17][O:16]2)[N:6]=1)=[N+]=[N-].[H][H]>[Pd]>[NH2:1][CH2:4][C:5]1[C:13]2[C:8](=[N:9][C:10]([F:14])=[CH:11][CH:12]=2)[N:7]([CH:15]2[CH2:20][CH2:19][CH2:18][CH2:17][O:16]2)[N:6]=1

Participants

4

Reactant 2

HCID 59529771HCID 59529771, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 59529781HCID 59529781, compound

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

Compound 2-4 (135 mg; 0.49 mmol) was hydrogenated in the presence of 10% Pd on carbon catalyst (25 mg) under 1 atmosphere hydrogen pressure (balloon) at room temperature. After 45 minutes LC-MS indicated that the reduction was complete. The reaction mixture was filtered through Celite, and the filtrate concentrated in vacuo to give the title product as a clear oil/solid. MS M+1=251. 1H NMR (CDCl3): 1.61 (m, 1H), 1.78 (m, 2H), 1.92 (dd, 1H), 2.03 (br m, 1H), 2.13 (br m, 1H), 2.60 (br m, 1H), 3.80 (br t, 1H), 4.12 (dd, 1H), 4.22 (br s, 2H), 5.93 (dd, 1H), 6.78 (dd, 1H), 8.21 (t, 1H).

Workup

  1. filtrationThe reaction mixture was filtered through Celite
  2. concentrationthe filtrate concentrated in vacuo

Sources & evidence

ORD record
ord-29302a2fef594c2f94c4c43a2dfe0890
Source dataset
uspto-grants-2013_03
Patent number
US08404856B2

Reaction notes

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