2,5-Dimethoxytetrahydrofuran → 4-[N-[1-[N-(furan-2-ylcarbonyl)amino]cyclohexanecarbonyl]amino]-1-[4-fluoro-2-(pyrrol-1-yl)phenyl]piperidin-3-ol

HRID 1392420Notes

Reaction equation

HRID 1392420 reaction equation
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]([NH:8][C:9]1([C:15]([NH:17][CH:18]2[CH2:23][CH2:22][N:21]([C:24]3[CH:29]=[CH:28][C:27]([F:30])=[CH:26][C:25]=3[NH2:31])[CH2:20][CH:19]2[OH:32])=[O:16])[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]1)=[O:7].CO[CH:35]1[CH2:39][CH2:38][CH:37](OC)O1>C(O)(=O)C>[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]([NH:8][C:9]1([C:15]([NH:17][CH:18]2[CH2:23][CH2:22][N:21]([C:24]3[CH:29]=[CH:28][C:27]([F:30])=[CH:26][C:25]=3[N:31]3[CH:35]=[CH:39][CH:38]=[CH:37]3)[CH2:20][CH:19]2[OH:32])=[O:16])[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]1)=[O:7]

Participants

4

Reactant 2

HCID 790982,5-DimethoxytetrahydrofuranHCID 693103034-[N-[1-[N-(furan-2-ylcarbonyl)amino]cyclohexanecarbonyl]amino]-1-(4-fluoro-2-aminophenyl)piperidin-3-ol

Product 1

HCID 693104454-[N-[1-[N-(furan-2-ylcarbonyl)amino]cyclohexanecarbonyl]amino]-1-[4-fluoro-2-(pyrrol-1-yl)phenyl]piperidin-3-ol

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

The mixture of 4-[N-[1-[N-(furan-2-ylcarbonyl)amino]cyclohexanecarbonyl]amino]-1-(4-fluoro-2-aminophenyl)piperidin-3-ol (3.0 g) obtained in Step 2 of Example 87 and 2,5-dimethoxytetrahydrofuran (0.96 ml) was refluxed in 80 ml of acetic acid for 1 hour. The reaction mixture was concentrated under reduced pressure. The resulting residue was diluted with 70 ml of dichloromethane and washed with a saturated sodium bicarbonate and brine. The resulting organic layer was dried and concentrated on sodium sulfate. The resulting residue was purified with column chromatography to give 1.8 g of the titled compound as white color.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. additionThe resulting residue was diluted with 70 ml of dichloromethane
  3. washwashed with a saturated sodium bicarbonate and brine
  4. customThe resulting organic layer was dried
  5. concentrationconcentrated on sodium sulfate
  6. customThe resulting residue was purified with column chromatography

Sources & evidence

ORD record
ord-7bd87e4dab8d44f9b987e53b011b475b
Source dataset
uspto-grants-2008_03
Patent number
US07342027B2

Reaction notes

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