Hydrochloric Acid → HCID 22915162, compound

HRID 1377559Notes

Reaction equation

HRID 1377559 reaction equation
[F:1][C:2]([Si](C)(C)C)([F:4])[F:3].[CH3:9][C:10]1[N:11]=[CH:12][S:13][C:14]=1[C:15]([C:17]1[S:21][CH:20]=[N:19][C:18]=1[CH3:22])=[O:16].[F-].C([N+](CCCC)(CCCC)CCCC)CCC.Cl.CC1C=CC(COC(NNC(C2C=NC=CN=2)=O)=O)=CC=1.[OH-].[K+]>O1CCCC1>[CH3:22][C:18]1[N:19]=[CH:20][S:21][C:17]=1[C:15]([C:14]1[S:13][CH:12]=[N:11][C:10]=1[CH3:9])([OH:16])[C:2]([F:4])([F:3])[F:1]

Participants

8

Reactant 6

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 478568p-tolylmethyl N-(pyrazine-2-carbonylamino)carbamateHCID 552549(Trifluoromethyl)trimethylsilaneHCID 2724141Tetrabutylammonium FluorideHCID 54262211HCID 54262211, compound

Product 1

HCID 22915162HCID 22915162, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

(Trifluoromethyl)trimethylsilane (494 μl) was added to a stirred solution of bis(4-methyl-5-thiazolyl) ketone (500 mg) in anhydrous tetrahydrofuran (20 ml) at room temperature. After 1 hour, tetrabutylammonium fluoride (300 mg) was added. The mixture was stirred for 2 hours and then 3M hydrochloric acid was added. After 10 minutes the reaction mixture was adjusted to pH10 by the addition of 5M potassium hydroxide. The organic phase was separated and then worked-up in the usual manner to give the title compound.

Workup

  1. customThe organic phase was separated

Sources & evidence

ORD record
ord-5c8d1113aca1406389cd37a7b96b90bd
Source dataset
uspto-grants-1997_09
Patent number
US05665747

Reaction notes

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