Trifluoroacetic acid → HCID 9824320, compound

HRID 379056Notes

Reaction equation

HRID 379056 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:47]=[CH:48][CH:49]=1)[O:5][C:6]1[CH:13]=[C:12]([C:14]([C:40]2[CH:45]=[CH:44][C:43]([Cl:46])=[CH:42][CH:41]=2)([OH:39])[C:15]2[N:16]=[CH:17][N:18](C(C3C=CC=CC=3)(C3C=CC=CC=3)C3C=CC=CC=3)[CH:19]=2)[CH:11]=[CH:10][C:7]=1[C:8]#[N:9].FC(F)(F)C(O)=O.C([SiH](CC)CC)C>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[C:4]([CH:47]=[CH:48][CH:49]=1)[O:5][C:6]1[CH:13]=[C:12]([C:14]([C:40]2[CH:45]=[CH:44][C:43]([Cl:46])=[CH:42][CH:41]=2)([OH:39])[C:15]2[NH:16][CH:17]=[N:18][CH:19]=2)[CH:11]=[CH:10][C:7]=1[C:8]#[N:9]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 21697000HCID 21697000, compound

Product 1

HCID 9824320HCID 9824320, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-(3-Chloro-phenoxy)-4-[(4-chloro-phenyl)-hydroxy-(1-trityl-1H-imidazol-4-yl)-methyl]-benzonitrile (0.269 g, 0.396 mmol), trifluoroacetic acid (5 mL), triethylsilane (0.050 mL, 3.17 mmol) was stirred in CH2Cl2 (5 mL) under Ar for 2 hr. The reaction mixture was concentrated in vacuo, diluted with EtOAc, washed with satd. NaHCO3 solution, water, brine, dried (MgSO4), concentrated and purified using SiO2 chromatography (1-1.5% MeOH/CH2Cl2 w NH4OH) to give the title compound. FAB MS (M+1)=436;

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. additiondiluted with EtOAc
  3. washwashed with satd
  4. dry with materialNaHCO3 solution, water, brine, dried (MgSO4)
  5. concentrationconcentrated
  6. custompurified

Sources & evidence

ORD record
ord-d76c91ba9e2c4baba0be5de82ad88294
Source dataset
uspto-grants-2001_10
Patent number
US06297239B1

Reaction notes

Loading…