Trifluoroacetic acid → HCID 67047497, compound

HRID 606911Notes

Reaction equation

HRID 606911 reaction equation
C(OC(=O)[NH:7][CH2:8][C:9]1[CH:14]=[C:13]([C:15]#[C:16][C:17]2[CH:18]=[N:19][CH:20]=[C:21]([C:23]#[N:24])[CH:22]=2)[CH:12]=[CH:11][C:10]=1[F:25])(C)(C)C.FC(F)(F)C(O)=O>ClCCl>[NH3:7].[NH2:7][CH2:8][C:9]1[CH:14]=[C:13]([C:15]#[C:16][C:17]2[CH:18]=[N:19][CH:20]=[C:21]([CH:22]=2)[C:23]#[N:24])[CH:12]=[CH:11][C:10]=1[F:25]

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67047955HCID 67047955, compound

Product 2

HCID 222AmmoniaHCID 67047497HCID 67047497, compoundYield 193.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Dissolve [5-(5-cyanopyridin-3-ylethynyl)-2-fluorobenzyl]carbamic acid tert-butyl ester, (prepared as described in EXAMPLE 144), (390 mg, 1.11 mmol) in dichloromethane (7.5 mL) and treat with trifluoroacetic acid (2.57 mL, 33.3 mmol). After stirring for 1.5 h, dilute with dichloromethane and wash with an aqueous saturated solution of sodium bicarbonate and an aqueous saturated solution of sodium chloride. Dry (sodium sulfate), filter, and concentrate. Purify the residue by silica gel chromatography, eluting with a gradient from 90:10 to 75:25 (98:2 dichloromethane:7 N ammonia in methanol):(9:2 acetonitrile:7 N ammonia in methanol), to give the title compound as a white crystalline solid (270 mg, 97%).

Workup

  1. washwash with an aqueous saturated solution of sodium bicarbonate
  2. dry with materialDry (sodium sulfate)
  3. filtrationfilter
  4. concentrationconcentrate
  5. customPurify the residue by silica gel chromatography
  6. washeluting with a gradient from 90:10 to 75:25 (98:2 dichloromethane:7 N ammonia in methanol)

Sources & evidence

ORD record
ord-cd12f96aaf1943b998cceffac4214e12
Source dataset
uspto-grants-2011_03
Patent number
US07915424B2

Reaction notes

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