HCID 86680513, compound → HCID 86680514, compound

HRID 1184595Notes

Reaction equation

HRID 1184595 reaction equation
[CH2:1]=[C:2]([C:4]1[N:5]=[CH:6][C:7]([O:10][C@H:11]2[CH2:32][N:14]3[CH2:15][CH2:16][N:17]([C:19](=[O:31])[CH2:20][C:21]4[CH:26]=[CH:25][CH:24]=[C:23]([C:27]([F:30])([F:29])[F:28])[CH:22]=4)[CH2:18][C@@H:13]3[CH2:12]2)=[N:8][CH:9]=1)[CH3:3]>O1CCCC1.[Pd]>[CH:2]([C:4]1[N:5]=[CH:6][C:7]([O:10][C@H:11]2[CH2:32][N:14]3[CH2:15][CH2:16][N:17]([C:19](=[O:31])[CH2:20][C:21]4[CH:26]=[CH:25][CH:24]=[C:23]([C:27]([F:30])([F:28])[F:29])[CH:22]=4)[CH2:18][C@@H:13]3[CH2:12]2)=[N:8][CH:9]=1)([CH3:3])[CH3:1]

Participants

4

Reactant 1

HCID 86680513HCID 86680513, compound

Product 1

HCID 86680514HCID 86680514, compoundYield 97.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A solution of the product from Example 152D (42 mg, 0.094 mmol) in tetrahydrofuran (4 mL) was added to 5% Pd/C (8.40 mg, 0.079 mmol) in a 50 mL pressure reactor, and the mixture was stirred for 30 minutes under hydrogen (30 psi) at ambient temperature. The mixture was filtered through a 0.45 micron filter, and the solvents were evaporated in vacuo to afford the title compound (41 mg, 97%). 1H NMR (300 MHz, CDCl3) 8 ppm 8.12 (s, 1H), 7.91 (d, J=1.3 Hz, 1H), 7.59-7.40 (m, 4H), 5.43-5.29 (m, 1H), 4.71 (dd, J=40.2, 12.7 Hz, 1H), 3.97-3.61 (m, 4H), 3.34-2.68 (m, 3H), 2.54-1.76 (m, 6H), 1.26 (dd, J=14.5, 8.8 Hz, 6H); MS (ESI) m/z 449 (M+H)+.

Workup

  1. filtrationThe mixture was filtered through a 0.45 micron
  2. filtrationfilter
  3. customthe solvents were evaporated in vacuo

Sources & evidence

ORD record
ord-dc8697ed4b8346928fe96146b947a3d9
Source dataset
uspto-grants-2014_03
Patent number
US08669255B2

Reaction notes

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