Hydrochloric Acid → HCID 18399753, compound

HRID 2184827Notes

Reaction equation

HRID 2184827 reaction equation
[NH:1]1[C:9]2[CH:8]=[CH:7][N:6]=[C:5]([N:10]3[CH2:15][CH2:14][N:13]([CH2:16][CH2:17][C:18]4[C:26]5[C:21](=[CH:22][CH:23]=[C:24]([CH:27]([C:29]6[N:30]=[CH:31][N:32](C(C7C=CC=CC=7)(C7C=CC=CC=7)C7C=CC=CC=7)[CH:33]=6)O)[CH:25]=5)[NH:20][CH:19]=4)[CH2:12][CH2:11]3)[C:4]=2[CH:3]=[CH:2]1.C([SiH](CC)CC)C.FC(F)(F)C(O)=O.C([O-])(O)=O.[Na+].Cl>ClCCl>[NH:30]1[C:29]([CH2:27][C:24]2[CH:25]=[C:26]3[C:21](=[CH:22][CH:23]=2)[NH:20][CH:19]=[C:18]3[CH2:17][CH2:16][N:13]2[CH2:14][CH2:15][N:10]([C:5]3[C:4]4[CH:3]=[CH:2][NH:1][C:9]=4[CH:8]=[CH:7][N:6]=3)[CH2:11][CH2:12]2)=[CH:33][N:32]=[CH:31]1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 516892Sodium BicarbonateHCID 18399704HCID 18399704, compound

Product 1

HCID 18399753HCID 18399753, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution, cooled to −5° C., of 1.9 mmol of the compound obtained in Step 1 and 9.5 mmol of triethylsilane in dichloromethane, is treated with a solution of 19 mmol of trifluoroacetic acid. After stirring at ambient temperature for 18 hours, the reaction mixture is treated with a saturated solution of NaHCO3, and then the organic phase is treated with a 2N HCl solution. The aqueous phase is rendered basic with 20% sodium hydroxide solution, and extraction with dichloromethane enables the expected product to be isolated after drying and concentrating the organic phase.

Workup

  1. extractionThe aqueous phase is rendered basic with 20% sodium hydroxide solution, and extraction with dichloromethane
  2. customto be isolated
  3. customafter drying
  4. concentrationconcentrating the organic phase

Sources & evidence

ORD record
ord-c87430c13183405991c9bbdb6f7a9141
Source dataset
uspto-grants-2002_06
Patent number
US06399616B1

Reaction notes

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