Hydrochloric Acid → HCID 178522467, compound

HRID 1392406Notes

Reaction equation

HRID 1392406 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[C:34]#[N:35])[CH2:24][CH:23]2[OH:36])=[O:20])[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1)=[O:11].[Cl-].[NH4+].[N-:39]=[N+:40]=[N-:41].[Na+].Cl>CN(C)C=O.O>[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[C:34]3[NH:41][N:40]=[N:39][N:35]=3)[CH2:24][CH:23]2[OH:36])=[O:20])[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1)=[O:11]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 69315111HCID 69315111, compound

Product 1

HCID 178522467HCID 178522467, compoundYield 15.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

To the solution of 4-[N-[1-[N-(benzofuran-2-ylcarbonyl)amino]cyclohexanecarbonyl]amino]-1-(2-cyanophenyl)piperidin-3-ol (700 mg, 1.43 mmol) obtained in Step 1 in 20 ml of dimethylformamide, were added ammonium chloride (769 mg) and sodium azide (934 mg). The reaction mixture was stirred for about 12 hours at 120° C. 20 ml of water was added to the reaction mixture, which was then acidified with a concentrated hydrochloride solution. The resulting solid was filtered and dissolved in dichloromethane. The resulting residue was purified with column chromatography to give 120 mg of the titled compound.

Workup

  1. filtrationThe resulting solid was filtered
  2. dissolutiondissolved in dichloromethane
  3. customThe resulting residue was purified with column chromatography

Sources & evidence

ORD record
ord-38bd5f1d89b44c499b70397044de93f8
Source dataset
uspto-grants-2008_03
Patent number
US07342027B2

Reaction notes

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