Sodium Carbonate → 4-[N-[1-[N-(furan-2-ylcarbonyl)amino]cyclohexanecarbonyl]amino]-1-(4-fluoro-2-methoxyacetylaminophenyl)piperidin-3-ol

HRID 1392416Notes

Reaction equation

HRID 1392416 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].C(=O)([O-])[O-].[Na+].[Na+].[CH3:39][O:40][CH2:41][C:42](Cl)=[O:43]>O1CCCC1>[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[NH:31][C:42](=[O:43])[CH2:41][O:40][CH3:39])[CH2:20][CH:19]2[OH:32])=[O:16])[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]1)=[O:7]

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 96623Methoxyacetyl chlorideHCID 693103034-[N-[1-[N-(furan-2-ylcarbonyl)amino]cyclohexanecarbonyl]amino]-1-(4-fluoro-2-aminophenyl)piperidin-3-ol

Product 1

HCID 693132144-[N-[1-[N-(furan-2-ylcarbonyl)amino]cyclohexanecarbonyl]amino]-1-(4-fluoro-2-methoxyacetylaminophenyl)piperidin-3-olYield 95.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The solution of 4-[N-[1-[N-(furan-2-ylcarbonyl)amino]cyclohexanecarbonyl]amino]-1-(4-fluoro-2-aminophenyl)piperidin-3-ol (1.0 g, 2.24 mmol) obtained in Step 2 in 30 ml of tetrahydrofuran was cooled to 0° C. Sodium carbonate (350 mg, 3.36 mmol) and methoxyacetyl chloride (0.53 mg, 5.82 mmol) was added to the reaction mixture, which was then stirred for 4 hours. 20 ml of ice water was added to the reaction mixture, which was then concentrated and extracted with 50 ml of ethyl acetate. The resulting organic layer was dried and concentrated on sodium sulfate. The resulting residue was crystallized with ethyl acetate to give 1.1 g of the titled compound.

Workup

  1. concentrationwas then concentrated
  2. extractionextracted with 50 ml of ethyl acetate
  3. customThe resulting organic layer was dried
  4. concentrationconcentrated on sodium sulfate
  5. customThe resulting residue was crystallized with ethyl acetate

Sources & evidence

ORD record
ord-da1062d4c4bc412a9c702370ee8cb98c
Source dataset
uspto-grants-2008_03
Patent number
US07342027B2

Reaction notes

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