Hydrochloric Acid → HCID 11270980, compound

HRID 969788Notes

Reaction equation

HRID 969788 reaction equation
C([O:8][CH2:9][C@H:10]([NH:22][C:23](=[O:40])[C@@H:24]([NH:30][C:31]1[O:32][C:33]2[CH:39]=[CH:38][CH:37]=[CH:36][C:34]=2[N:35]=1)[CH2:25][C:26]([CH3:29])([CH3:28])[CH3:27])[CH2:11][N:12]1[C:20]2[C:15](=[CH:16][C:17]([F:21])=[CH:18][CH:19]=2)[CH2:14][CH2:13]1)C1C=CC=CC=1.Cl.[H][H]>CO.O1CCOCC1.[Pd]>[F:21][C:17]1[CH:16]=[C:15]2[C:20](=[CH:19][CH:18]=1)[N:12]([CH2:11][C@@H:10]([NH:22][C:23](=[O:40])[C@@H:24]([NH:30][C:31]1[O:32][C:33]3[CH:39]=[CH:38][CH:37]=[CH:36][C:34]=3[N:35]=1)[CH2:25][C:26]([CH3:29])([CH3:28])[CH3:27])[CH2:9][OH:8])[CH2:13][CH2:14]2

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 11466908HCID 11466908, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 11270980HCID 11270980, compoundYield 58.5%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 312751,4-DioxaneSolvent

Procedure

The title compound of example 6 (34 mg, 70 μmol) was dissolved in MeOH (3 mL) and treated with 4 M HCl in dioxane (0.5 mL). The reaction was then treated with 10% Pd/C (7 mg) and the atmosphere was exchanged for hydrogen by sparging the solution with a needle and a balloon. After 2 h under a hydrogen balloon, the atmosphere was exchanged back to nitrogen and the catalyst was removed by filtration through celite. The solvent was removed and the residue was purified by preperative reverse phase HPLC to afford the title compound as a gum (18.6 mg, 47%); 1H NMR (CDCl3, 400 MHz) δ 0.97 (s, 9H), 1.69 (dd, 1H, J1=9.0, J2=14.5), 1.81 (dd, 1H, J1=3.4, J2=14.5), 2.71-2.90 (m, 2H), 3.04-3.16 (m, 1H), 3.19-3.31 (m, 2H), 3.40-3.50 (m, 1H), 3.66 (d, 1H, J=5.2), 4.13-4.21 (m, 1H), 4.38 (dd, 1H, J1=3.4, J2=9.0), 6.44-6.52 (m, 1H), 6.59-6.66 (m, 1H), 6.70-6.74 (m, 1H), 7.14 (dd, 1H, J1=J2=7.7), 7.23 (dd, 1H, J1J2=7.6), 7.30 (d, 1H, J=7.8), 7.33 (d, 1H, J=8.0); HPLC-MS calcd. for C25H31FN4O3 (M+H+) 455.2, found 455.5.

Workup

  1. customby sparging the solution with a needle
  2. customthe catalyst was removed by filtration through celite
  3. customThe solvent was removed
  4. customthe residue was purified by preperative reverse phase HPLC

Sources & evidence

ORD record
ord-538cbdd1bbba4a9193cdb272ac69e4a4
Source dataset
uspto-grants-2007_12
Patent number
US07307095B2

Reaction notes

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