Dichloromethane → HCID 69226259, compound

HRID 1027901Notes

Reaction equation

HRID 1027901 reaction equation
[NH2:1][C:2]1[N:3]=[C:4]([N:18]2[CH2:26][CH:25]3[CH:20]([N:21]([C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[CH2:22][CH2:23][CH2:24]3)[CH2:19]2)[C:5]2[CH2:12][CH2:11][O:10][C:9]3[CH:13]=[C:14](I)[CH:15]=[CH:16][C:8]=3[C:6]=2[N:7]=1.C(Cl)Cl.C(N(CC)CC)C.[C]=O>CO>[NH2:1][C:2]1[N:3]=[C:4]([N:18]2[CH2:26][CH:25]3[CH:20]([N:21]([C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[CH2:22][CH2:23][CH2:24]3)[CH2:19]2)[C:5]2[CH2:12][CH2:11][O:10][C:9]3[CH:13]=[C:14]([C:27]([O:29][CH3:30])=[O:28])[CH:15]=[CH:16][C:8]=3[C:6]=2[N:7]=1

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 8471TriethylamineHCID 86621901HCID 86621901, compoundHCID 178418416HCID 178418416, compound

Product 1

HCID 69226259HCID 69226259, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of the product from Example 102A (55 mg, 0.098 mmol), PdCl2(pddf).CH2Cl2 (4 mg, 0.0049 mmol), triethylamine (0.027 mL, 0.19 mmol) and MeOH (2 mL) was heated at 100° C. in an atmosphere of carbon monoxide at a pressure of 60 psi for 3 hours. The mixture was cooled and filtered to remove the solids. The filtrate was concentrated and purified by chromatography on silica gel using a gradient of 4:1 to 0:1 CH2Cl2:EtOAc to provide the title compound. 1H NMR (CDCl3) δ 1.31-1.43 (m, 1H), 1.49 (s, 9H), 1.54-1.86 (m, 4H), 2.21-2.33 (m, 1H), 2.54-2.68 (m, 1H), 2.75-2.89 (m, 2H), 3.45 (d, J=11.1 Hz, 1H), 3.60-3.78 (m, 2H), 3.85-3.92 (m, 1H), 3.94 (s, 3H), 4.01-4.10 (m, 1H), 4.50-4.68 (m, 2H), 4.79 (s, 2H), 7.80 (d, J=1.6 Hz, 1H), 7.98 (dd, J=7.9, 1.6 Hz, 1H), 8.12 (d, J=8.3 Hz, 1H);

Workup

  1. temperatureThe mixture was cooled
  2. filtrationfiltered
  3. customto remove the solids
  4. concentrationThe filtrate was concentrated
  5. custompurified by chromatography on silica gel using a gradient of 4:1 to 0:1 CH2Cl2

Sources & evidence

ORD record
ord-0f6dd2c5f8044e6f8a637fd331d3980e
Source dataset
uspto-grants-2014_05
Patent number
US08735411B2

Reaction notes

Loading…