4-Methylmorpholine → HCID 117772597, compound

HRID 2201583Notes

Reaction equation

HRID 2201583 reaction equation
[CH2:1]([O:8][C:9]1[C:10]([C:41]([OH:43])=O)=[N:11][C:12]([C:15]2[C:16]([N:35]([CH3:40])[S:36]([CH3:39])(=[O:38])=[O:37])=[CH:17][C:18]3[O:22][C:21]([C:23]4[CH:28]=[CH:27][C:26]([F:29])=[CH:25][CH:24]=4)=[C:20]([C:30](=[O:33])[NH:31][CH3:32])[C:19]=3[CH:34]=2)=[CH:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CN1CCOCC1.C(OC(Cl)=O)C.[F:57][C:58]1[CH:63]=[CH:62][C:61]([C@H:64]([NH2:66])[CH3:65])=[CH:60][CH:59]=1>C1COCC1>[CH2:1]([O:8][C:9]1[C:10]([C:41]([NH:66][C@@H:64]([C:61]2[CH:62]=[CH:63][C:58]([F:57])=[CH:59][CH:60]=2)[CH3:65])=[O:43])=[N:11][C:12]([C:15]2[C:16]([N:35]([CH3:40])[S:36]([CH3:39])(=[O:37])=[O:38])=[CH:17][C:18]3[O:22][C:21]([C:23]4[CH:24]=[CH:25][C:26]([F:29])=[CH:27][CH:28]=4)=[C:20]([C:30](=[O:33])[NH:31][CH3:32])[C:19]=3[CH:34]=2)=[CH:13][CH:14]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 79724-MethylmorpholineHCID 10928Ethyl chloroformateHCID 6950187(1R)-(+)-1-(4-Fluorophenyl)ethylamineHCID 117771339HCID 117771339, compound

Product 1

HCID 117772597HCID 117772597, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

3-(benzyloxy)-6-(2-(4-fluorophenyl)-3-(methylcarbamoyl)-6-(N-methylmethylsulfonamido)benzofuran-5-yl)picolinic acid (110 mg, 0.18 mmol) was suspended in THF (2 ml), cooled to 0° C., then 4-methylmorpholine (55.3 mg, 0.55 mmol) and ethylchloroformate (27.7 mg, 0.26 mmol) were added. The resulting mixture was stirred at 0° C. for 1 h, then (R)-1-(4-fluorophenyl)ethylamine was added. The reaction was warmed to RT and stirred for 1 h, then concentrated in vacuo. The resulting residue was purified using column chromatography (eluted with 0-5% MeOH/DCM) to provide (R)-3-(benzyloxy)-6-(2-(4-fluorophenyl)-3-(methylcarbamoyl)-6-(N-methylmethylsulfonamido)benzofuran-5-yl)-N-(1-(4-fluorophenyl)ethyl)picolinamide (100 mg, yield: 76%). MS (M+H)+: 724.

Workup

  1. temperatureThe reaction was warmed to RT
  2. stirringstirred for 1 h
  3. concentrationconcentrated in vacuo
  4. customThe resulting residue was purified
  5. washcolumn chromatography (eluted with 0-5% MeOH/DCM)

Sources & evidence

ORD record
ord-fd0bd1345ee14231aa0d769a298fd3cc
Source dataset
uspto-grants-2016_06
Patent number
US09364482B2

Reaction notes

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