Trifluoroacetic acid → HCID 21638785, compound

HRID 392775Notes

Reaction equation

HRID 392775 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][N:11]([C:14]([C:16]2[NH:17][C:18]3[C:23]([CH:24]=2)=[CH:22][C:21]([Cl:25])=[CH:20][CH:19]=3)=[O:15])[CH2:10][CH2:9]1)=O)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[Cl:25][C:21]1[CH:22]=[C:23]2[C:18](=[CH:19][CH:20]=1)[NH:17][C:16]([C:14]([N:11]1[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]1)=[O:15])=[CH:24]2

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 55556362HCID 55556362, compound

Product 1

HCID 21638785HCID 21638785, compoundYield 95.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The product from Step A (11 g) was suspended in CH2Cl2 (75 mL), and TFA was added dropwise (75 mL). The resulting solution was stirred overnight at ambient temperature. The reaction solution was concentrated under reduced pressure, and the resulting residue was dissolved in CH2Cl2 (100 mL). Saturated aqueous NaHCO3 (100 mL) was added slowly with stirring. After 20 min the organic layer was separated, washed with water (10 mL) and then brine (30 mL), and dried over Na2SO4. The organic layer was then concentrated under reduced pressure and purified via silica gel chromatography (0-35% methanol/dichloromethane) to give the title compound (7.6 g). MS (electrospray): exact mass calculated for C13H14ClN3O, 263.08; m/z found, 264.1 [M+H]+.

Workup

  1. concentrationThe reaction solution was concentrated under reduced pressure
  2. dissolutionthe resulting residue was dissolved in CH2Cl2 (100 mL)
  3. additionSaturated aqueous NaHCO3 (100 mL) was added slowly
  4. stirringwith stirring
  5. customAfter 20 min the organic layer was separated
  6. washwashed with water (10 mL)
  7. dry with materialbrine (30 mL), and dried over Na2SO4
  8. concentrationThe organic layer was then concentrated under reduced pressure
  9. custompurified via silica gel chromatography (0-35% methanol/dichloromethane)

Sources & evidence

ORD record
ord-5498b006a54c47e89c1a1947b7302cf7
Source dataset
uspto-grants-2004_10
Patent number
US06803362B2

Reaction notes

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