Trifluoroacetic acid → HCID 68718723, compound

HRID 1161990Notes

Reaction equation

HRID 1161990 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8]([NH:11][C:12]1[CH:13]=[C:14]([N:21]2[CH2:26][CH2:25][N:24](C(OC(C)(C)C)=O)[CH2:23][CH2:22]2)[C:15]2[O:19][CH:18]=[CH:17][C:16]=2[CH:20]=1)(=[O:10])=[O:9].C(O)(C(F)(F)F)=O>C(Cl)Cl>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8]([NH:11][C:12]1[CH:13]=[C:14]([N:21]2[CH2:22][CH2:23][NH:24][CH2:25][CH2:26]2)[C:15]2[O:19][CH:18]=[CH:17][C:16]=2[CH:20]=1)(=[O:9])=[O:10]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acid2×HCID 69630494HCID 69630494, compound2×

Product 1

HCID 68718723HCID 68718723, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

tert-Butyl 4-(5-{[(2-chlorophenyl)sulfonyl]amino}-1-benzofuran-7-yl)piperazine-1-carboxylate (0.66 g, 1.34 mmol; Intermediate 19) was dissolved in DCM (5 mL) and TFA was added (30% solution of TFA in DCM; 5 mL) and the mixture was stirred for 30 min. The solvents were evaporated. The residue was dissolved in water, pH adjusted to pH 8 and extracted with EtOAc. The organic layer was dried and evaporated to give 0.41 g (80%) of the title product that was used in the next step without further purification. HPLC purity 93%, RT=1.61 min (System A; 10-97% MeCN over 3 min).

Workup

  1. customThe solvents were evaporated
  2. dissolutionThe residue was dissolved in water
  3. extractionextracted with EtOAc
  4. customThe organic layer was dried
  5. customevaporated

Sources & evidence

ORD record
ord-e8da6707bd834617a2ed36800e28dc40
Source dataset
uspto-grants-2010_10
Patent number
US07820675B2

Reaction notes

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