Potassium Iodide → tert-butyl 3-(2-(2-(2-(((6-((4-(piperidin-1-yl)-2-((1-(3-(trifluoromethyl)phenyl)-1H-pyrazol-3-yl)carbamoyl)-phenyl)carbamoyl)pyridin-2-yl)methyl)(methyl)amino)ethoxy)ethoxy)ethoxy)propanoate

HRID 926875Notes

Reaction equation

Cl[CH2:2][C:3]1[N:8]=[C:7]([C:9]([NH:11][C:12]2[CH:17]=[CH:16][C:15]([N:18]3[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]3)=[CH:14][C:13]=2[C:24](=[O:41])[NH:25][C:26]2[CH:30]=[CH:29][N:28]([C:31]3[CH:36]=[CH:35][CH:34]=[C:33]([C:37]([F:40])([F:39])[F:38])[CH:32]=3)[N:27]=2)=[O:10])[CH:6]=[CH:5][CH:4]=1.[CH3:42][NH:43][CH2:44][CH2:45][O:46][CH2:47][CH2:48][O:49][CH2:50][CH2:51][O:52][CH2:53][CH2:54][C:55]([O:57][C:58]([CH3:61])([CH3:60])[CH3:59])=[O:56].[I-].[K+].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O.O>[N:18]1([C:15]2[CH:16]=[CH:17][C:12]([NH:11][C:9]([C:7]3[N:8]=[C:3]([CH2:2][N:43]([CH3:42])[CH2:44][CH2:45][O:46][CH2:47][CH2:48][O:49][CH2:50][CH2:51][O:52][CH2:53][CH2:54][C:55]([O:57][C:58]([CH3:60])([CH3:59])[CH3:61])=[O:56])[CH:4]=[CH:5][CH:6]=3)=[O:10])=[C:13]([C:24](=[O:41])[NH:25][C:26]3[CH:30]=[CH:29][N:28]([C:31]4[CH:36]=[CH:35][CH:34]=[C:33]([C:37]([F:40])([F:39])[F:38])[CH:32]=4)[N:27]=3)[CH:14]=2)[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23]1

Participants

Conditions

Temperature: 70 °C

Procedure

Into a 50-mL round bottom flask, was placed a solution of 6-(chloromethyl)-N-(4-(piperidin-1-yl)-2-((1-(3-(trifluoromethyl)phenyl)-1H-pyrazol-3-yl)carbamoyl)phenyl)picolinamide (170 mg, 0.29 mmol, 1.00 equiv) in N,N-dimethylformamide (5 mL), tert-butyl 3-(2-(2-(2-(methylamino)ethoxy)ethoxy)ethoxy)-propanoate (255 mg, 0.88 mmol, 3.00 equiv), potassium iodide (24.2 mg, 0.15 mmol, 0.50 equiv), and potassium carbonate (79.5 mg, 0.58 mmol, 1.97 equiv). The resulting solution was stirred for 2.5 h at 70° C. in an oil bath. The reaction progress was monitored by LCMS. The resulting solution was diluted with 50 mL of water. The resulting solution was extracted with 3×50 mL of ethyl acetate and the organic layers combined. The resulting mixture was washed with 3×50 mL of brine, dried over anhydrous sodium sulfate, and concentrated under vacuum. This resulted in

Workup

customInto a 50-mL round bottom flask, was placed
extractionThe resulting solution was extracted with 3×50 mL of ethyl acetate
washThe resulting mixture was washed with 3×50 mL of brine
dry with materialdried over anhydrous sodium sulfate
concentrationconcentrated under vacuum
customThis resulted in

Sources & evidence

ORD record: ord-16a2e40daeb64d6fb61e88365a89ab82
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09289430B2

Reaction notes

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