HCID 19691260, compound → HCID 25071321, compound

HRID 1027868Notes

Reaction equation

HRID 1027868 reaction equation
CS([C:5]1[C:6]2[CH2:16][CH2:15][CH2:14][C:13]3[CH:17]=[CH:18][CH:19]=[CH:20][C:12]=3[C:7]=2[N:8]=[C:9]([NH2:11])[N:10]=1)(=O)=O.C(O[C:29]([N:31]1[CH2:35][CH2:34][CH:33]2[CH2:36][NH:37][CH2:38][CH:32]12)=O)C1C=CC=CC=1>C(O)=O.CO.[OH-].[OH-].[Pd+2]>[CH3:29][N:31]1[CH2:35][CH2:34][C@@H:33]2[CH2:36][N:37]([C:5]3[C:6]4[CH2:16][CH2:15][CH2:14][C:13]5[CH:17]=[CH:18][CH:19]=[CH:20][C:12]=5[C:7]=4[N:8]=[C:9]([NH2:11])[N:10]=3)[CH2:38][C@H:32]12

Participants

6

Reactant 2

HCID 19691260HCID 19691260, compoundHCID 69226365HCID 69226365, compound

Product 1

HCID 25071321HCID 25071321, compound

Reagents, catalysts & solvents 3

HCID 9942167Palladium hydroxideCatalystHCID 284Formic AcidSolventHCID 887MethanolSolvent

Procedure

The title compound was prepared using the procedure described in Example 1F, substituting the product from Example 3A for the product from Example 1C, and substituting the product from Example 15B for the product from Example 1E. The resulting intermediate was refluxed for 16 hours in 4.4% formic acid in methanol with the presence of Pd(OH)2 (5% mol). The mixture was concentrated under reduced pressure and the residue was chromatographed on silica gel eluting with 3% (9:1 MeOH: NH4OH) in dichloromethane to provide the title compound. 1H NMR (CDCl3) δ 1.71-1.84 (m, 1H), 2.04-2.10 (m, 1H), 2.15-2.20 (m, 3H), 2.31-2.40 (m, 1H), 2.38 (s, 3H), 2.51-2.56 (m, 1H), 2.64 (t, J=6.44 Hz, 2H), 2.83 (m, 2H), 3.14-3.21 (m, 1H), 3.60-3.77 (m, 4H), 4.85 (s, 2H), 7.18-7.21 (m, 1H), 7.31-7.34 (m, 2H), 7.73-7.77 (m, 1H). MS (M+H)+ m/z 336.

Workup

  1. customThe title compound was prepared
  2. concentrationThe mixture was concentrated under reduced pressure
  3. customthe residue was chromatographed on silica gel eluting with 3% (9:1 MeOH: NH4OH) in dichloromethane

Sources & evidence

ORD record
ord-874caa858ddf4a2db3e9ecb2ceb94a95
Source dataset
uspto-grants-2014_05
Patent number
US08735411B2

Reaction notes

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