Hydrochloric Acid → HCID 18399753, compound

HRID 1019011Notes

Reaction equation

HRID 1019011 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-d03c6e2f857e48dd862718b4d9d0336d
Source dataset
uspto-grants-2002_11
Patent number
US06486171B2

Reaction notes

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