Trifluoroacetic acid → HCID 10162803, compound

HRID 989681Notes

Reaction equation

HRID 989681 reaction equation
C([C:3]1[CH:7]=[CH:6][O:5][N:4]=1)=O.[C:8]([C:10]1[CH:11]=[CH:12][C:13]2[N:19]([CH2:20]C3OC=NC=3)[CH2:18][C@@H:17]([CH2:26][C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[N:16]([S:33]([CH2:36][CH2:37][N:38]([CH3:40])[CH3:39])(=[O:35])=[O:34])[CH2:15][C:14]=2[CH:41]=1)#[N:9].C(O)(C(F)(F)F)=O.C([SiH](CC)CC)C.C([O-])(O)=O.[Na+]>C(Cl)Cl>[C:8]([C:10]1[CH:11]=[CH:12][C:13]2[N:19]([CH2:20][C:6]3[O:5][N:4]=[CH:3][CH:7]=3)[CH2:18][C@@H:17]([CH2:26][C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[N:16]([S:33]([CH2:36][CH2:37][N:38]([CH3:40])[CH3:39])(=[O:34])=[O:35])[CH2:15][C:14]=2[CH:41]=1)#[N:9]

Participants

7

Reactant 5

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 516892Sodium BicarbonateHCID 10140618(R)-7-Cyano-4-[[2-(dimethylamino)ethyl]sulfonyl]-2,3,4,5-tetrahydro-1-(5-oxazolylmethyl)-3-(phenylmethyl)-1H-1,4-benzodiazepineHCID 183730781,2-Oxazole-3-carbaldehyde

Product 1

HCID 10162803HCID 10162803, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of 3-formylisoxazole (19.4 mg, 0.2 mmol) and Compound B of Example 25 (39.9 mg, 0.1 mmol) in DCM (0.5 mL) at rt was added TFA (45 mg, 0.4 mmol), followed by triethylsilane (35 mg, 0.3 mmol). The resulting mixture was stirred at rt for 1 hour, neutrallized with NaHCO3 solution and extracted with DCM (2×5 mL). The combined extract was dried over Na2SO4 and concentrated. The residue was purified by flash column chromatography (SiO2; ethyl acetate: methanol ammonia/100:10:0.1) to afford the title compound, 45 mg (87%). MS: m/e (M+H)+=480.

Workup

  1. extractionextracted with DCM (2×5 mL)
  2. extractionThe combined extract
  3. dry with materialwas dried over Na2SO4
  4. concentrationconcentrated
  5. customThe residue was purified by flash column chromatography (SiO2; ethyl acetate: methanol ammonia/100:10:0.1)

Sources & evidence

ORD record
ord-b73c8993eebe46619d3c02a993624fe3
Source dataset
uspto-grants-2002_10
Patent number
US06458783B1

Reaction notes

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