Potassium Iodide → Tert-butyl 3-(2-(2-(2-((3-((2-(4-((3-(trifluoromethyl)benzyl)carbamoyl)pyridin-2-yl)-4-(piperidin-1-yl)phenyl)-carbamoyl)benzyl)(methyl)amino)ethoxy)ethoxy)ethoxy)propanoate

HRID 1408092Notes

Reaction equation

HRID 1408092 reaction equation
[CH3:1][NH:2][CH2:3][CH2:4][O:5][CH2:6][CH2:7][O:8][CH2:9][CH2:10][O:11][CH2:12][CH2:13][C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15].C(=O)([O-])[O-].[K+].[K+].[I-].[K+].[F:29][C:30]([F:71])([F:70])[C:31]1[CH:32]=[C:33]([CH:67]=[CH:68][CH:69]=1)[CH2:34][NH:35][C:36](=[O:66])[C:37]1[CH:42]=[CH:41][N:40]=[C:39]([C:43]2[CH:48]=[C:47]([N:49]3[CH2:54][CH2:53][CH2:52][CH2:51][CH2:50]3)[CH:46]=[CH:45][C:44]=2[NH:55][C:56](=[O:65])[C:57]2[CH:62]=[CH:61][CH:60]=[C:59]([CH2:63]Br)[CH:58]=2)[CH:38]=1>CN(C)C=O>[F:29][C:30]([F:71])([F:70])[C:31]1[CH:32]=[C:33]([CH:67]=[CH:68][CH:69]=1)[CH2:34][NH:35][C:36]([C:37]1[CH:42]=[CH:41][N:40]=[C:39]([C:43]2[CH:48]=[C:47]([N:49]3[CH2:54][CH2:53][CH2:52][CH2:51][CH2:50]3)[CH:46]=[CH:45][C:44]=2[NH:55][C:56]([C:57]2[CH:58]=[C:59]([CH:60]=[CH:61][CH:62]=2)[CH2:63][N:2]([CH3:1])[CH2:3][CH2:4][O:5][CH2:6][CH2:7][O:8][CH2:9][CH2:10][O:11][CH2:12][CH2:13][C:14]([O:16][C:17]([CH3:19])([CH3:18])[CH3:20])=[O:15])=[O:65])[CH:38]=1)=[O:66]

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 53662991Methylamino-PEG3-t-butyl esterHCID 665867752-(2-(3-(bromomethyl)benzamido)-5-(piperidin-1-yl)phenyl)-N-(3-(trifluoromethyl)benzyl)isonicotinamide

Product 1

HCID 66586756Tert-butyl 3-(2-(2-(2-((3-((2-(4-((3-(trifluoromethyl)benzyl)carbamoyl)pyridin-2-yl)-4-(piperidin-1-yl)phenyl)-carbamoyl)benzyl)(methyl)amino)ethoxy)ethoxy)ethoxy)propanoate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

Into a 8-mL round-bottom flask, was placed a solution of tert-butyl 3-(2-(2-(2-(methylamino)ethoxy)ethoxy)ethoxy)propanoate (89.3 mg, 0.31 mmol, 1.00 equiv) in N,N-dimethylformamide (6 mL), potassium carbonate (84.7 mg, 0.61 mmol, 1.99 equiv), potassium iodide (10.2 mg, 0.06 mmol, 0.20 equiv), and N-(3-(trifluoromethyl)benzyl)-2-(2-(3-(bromomethyl)benzamido)-5-(piperidin-1-yl)phenyl)isonicotinamide (200 mg, 0.31 mmol, 1.00 equiv). The resulting solution was stirred overnight at 70° C. The solids were filtered out. The resulting mixture was concentrated under vacuum. The residue was dissolved in 20 mL of dichloromethane. The resulting mixture was washed with 2×20 mL of water. The resulting mixture was washed with 1×20 mL of brine, dried over sodium sulfate, and concentrated under vacuum. This resulted in 264 mg (crude) of product as yellow oil.

Workup

  1. customInto a 8-mL round-bottom flask, was placed
  2. filtrationThe solids were filtered out
  3. concentrationThe resulting mixture was concentrated under vacuum
  4. dissolutionThe residue was dissolved in 20 mL of dichloromethane
  5. washThe resulting mixture was washed with 2×20 mL of water
  6. washThe resulting mixture was washed with 1×20 mL of brine
  7. dry with materialdried over sodium sulfate
  8. concentrationconcentrated under vacuum
  9. customThis resulted in 264 mg (crude) of product as yellow oil

Sources & evidence

ORD record
ord-43d99710000e4b64adc118b9ac6105aa
Source dataset
uspto-grants-2014_12
Patent number
US08916569B2

Reaction notes

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