Ethyl orthoformate → 4-[N-[1-[N-(benzofuran-2-ylcarbonyl)amino]cyclohexanecarbonyl]amino]-1-[2-(tetrazol-1-yl)phenyl]piperidin-3-ol

HRID 1392396Notes

Reaction equation

HRID 1392396 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[CH:3]=[C:2]1[C:10]([NH:12][C:13]1([C:19]([NH:21][CH:22]2[CH2:27][CH2:26][N:25]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=3[NH2:34])[CH2:24][CH:23]2[OH:35])=[O:20])[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1)=[O:11].[N-:36]=[N+:37]=[N-:38].[Na+].[CH:40](OCC)(OCC)OCC>C(O)(=O)C>[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[CH:3]=[C:2]1[C:10]([NH:12][C:13]1([C:19]([NH:21][CH:22]2[CH2:27][CH2:26][N:25]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=3[N:34]3[CH:40]=[N:38][N:37]=[N:36]3)[CH2:24][CH:23]2[OH:35])=[O:20])[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1)=[O:11]

Participants

5

Reactant 3

HCID 31214Ethyl orthoformateHCID 33557Sodium AzideHCID 693129984-[N-[1-[N-(benzofuran-2-ylcarbonyl)amino]cyclohexanecarbonyl]amino]-1-(2-aminophenyl)piperidin-3-ol

Product 1

HCID 693132254-[N-[1-[N-(benzofuran-2-ylcarbonyl)amino]cyclohexanecarbonyl]amino]-1-[2-(tetrazol-1-yl)phenyl]piperidin-3-olYield 28.3%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

The mixture of 4-[N-[1-[N-(benzofuran-2-ylcarbonyl)amino]cyclohexanecarbonyl]amino]-1-(2-aminophenyl)piperidin-3-one (2 g, 4 mmol) obtained in Step 2 of Example 43, sodium azide (NaN3; 409 mg, 6.2 mmol) and triethyl orthoformate (1.1 ml, 6.7 mmol) was refluxed in 10 ml of acetic acid for about 4 hours. The reaction mixture was cooled to room temperature. 10 ml of ice water was added to the reaction mixture, which was then stirred for about 48 hours. The resulting residue was filtered and dried to give 0.6 g of the titled compound.

Workup

  1. filtrationThe resulting residue was filtered
  2. customdried

Sources & evidence

ORD record
ord-dffbd1a96076496faabe7aed1f424806
Source dataset
uspto-grants-2008_03
Patent number
US07342027B2

Reaction notes

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