Fluoroacetyl chloride → HCID 46174436, compound

HRID 2035675Notes

Reaction equation

HRID 2035675 reaction equation
[F:1][CH2:2][C:3](Cl)=[O:4].[N:6]1[N:7]=[C:8]([C:15]2[CH:24]=[CH:23][C:22]3[C:17](=[C:18]([O:25][CH2:26][C:27]([CH3:31])([CH3:30])[CH2:28][NH2:29])[CH:19]=[CH:20][CH:21]=3)[N:16]=2)[N:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=12.C(N(C(C)C)CC)(C)C>C(Cl)Cl>[N:6]1[N:7]=[C:8]([C:15]2[CH:24]=[CH:23][C:22]3[C:17](=[C:18]([O:25][CH2:26][C:27]([CH3:31])([CH3:30])[CH2:28][NH:29][C:3](=[O:4])[CH2:2][F:1])[CH:19]=[CH:20][CH:21]=3)[N:16]=2)[N:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=12

Participants

5

Reactant 3

HCID 9663Fluoroacetyl chlorideHCID 81531DiisopropylethylamineHCID 58303707HCID 58303707, compound

Product 1

HCID 46174436HCID 46174436, compoundYield 34%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-Fluoroacetyl chloride (12 mg, 0.13 mmol) was added to a stirred solution of 3-(2-([1,2,4]triazolo[4,3-a]pyridin-3-yl)quinolin-8-yloxy)-2,2-dimethylpropan-1-amine (prepared according to Example 18; 30 mg, 0.086 mmol) and diisopropylethyl amine (45 μL, 0.26 mmol) in DCM (2 mL) at 0° C. After 30 minutes, the reaction was quenched with saturated aqueous bicarbonate (5 mL), extracted into EtOAc, washed with water, dried over Na2SO4 followed by concentration in vacuo. The resulting oil was purified by flash column chromatography (silica gel), eluting with 100% EtOAc (Biotage) to give the desired product (12 mg, 0.029 mmol, 34% yield) as a white solid. MS ESI (+) m/z 408.2 (M+1) detected.

Workup

  1. customthe reaction was quenched with saturated aqueous bicarbonate (5 mL)
  2. extractionextracted into EtOAc
  3. washwashed with water
  4. dry with materialdried over Na2SO4
  5. concentrationfollowed by concentration in vacuo
  6. customThe resulting oil was purified by flash column chromatography (silica gel)
  7. washeluting with 100% EtOAc (Biotage)

Sources & evidence

ORD record
ord-9f4a566fb4904bf9b617e429ec63967d
Source dataset
uspto-grants-2013_11
Patent number
US08575145B2

Reaction notes

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