HCID 71486919, compound → HCID 71144426, compound

HRID 1622566Notes

Reaction equation

HRID 1622566 reaction equation
[CH2:1]([C:4]1[C:5]([C@H:10]([C:21]2[CH:26]=[CH:25][C:24]([C:27]([F:30])([F:29])[F:28])=[CH:23][CH:22]=2)[NH:11][C:12]([NH:14][C:15]2[CH:16]=[N:17][CH:18]=[CH:19][CH:20]=2)=[O:13])=[N:6][CH:7]=[CH:8][CH:9]=1)[CH:2]=[CH2:3]>CO.[Pd]>[CH2:1]([C:4]1[C:5]([C@H:10]([C:21]2[CH:22]=[CH:23][C:24]([C:27]([F:29])([F:30])[F:28])=[CH:25][CH:26]=2)[NH:11][C:12]([NH:14][C:15]2[CH:16]=[N:17][CH:18]=[CH:19][CH:20]=2)=[O:13])=[N:6][CH:7]=[CH:8][CH:9]=1)[CH2:2][CH3:3]

Participants

4

Reactant 1

HCID 71486919HCID 71486919, compound

Product 1

HCID 71144426HCID 71144426, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of (S)-1-((3-allylpyridin-2-yl)(4-(trifluoromethyl)phenyl)-methyl)-3-(pyridin-3-yl)urea (Example 43) (0.055 g, 0.133 mmol) and Pd (10 wt % on carbon, 0.020 g, 0.133 mmol) in MeOH was hydrogenated under H2 (1 atm) at rt for 4 h. The catalyst was filtered off, and the filtrate was concentrated to give the title compound as a white solid. 1H NMR (300 MHz, d4-MeOH): δ ppm 8.60-8.38 (m, 2H), 8.12 (d, J=4.4 Hz, 1H), 7.93 (d, J=8.3 Hz, 1H), 7.74-7.43 (m, 5H), 7.40-7.21 (m, 2H), 6.42 (s, 1H), 2.89-2.51 (m, 2H), 1.74-1.35 (m, 2H), 0.95 (t, J=7.2 Hz, 3H). MS (ESI pos. ion) m/z: 415.0 (M+H).

Workup

  1. filtrationThe catalyst was filtered off
  2. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-bd7e273f52d043919d5eace49a31a2bc
Source dataset
uspto-grants-2014_07
Patent number
US08778941B2

Reaction notes

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