Trifluoroacetic acid → HCID 86686848, compound

HRID 402952Notes

Reaction equation

HRID 402952 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([C:14]2[CH:15]=[N:16][C:17]([NH:20][C:21]3[C:22]4[N:23]([CH:54]=[CH:55][N:56]=4)[CH:24]=[C:25]([C:27]4[CH:32]=[CH:31][CH:30]=[C:29]([N:33]5[N:42]=[CH:41][C:40]6[C:35](=[C:36]([F:47])[CH:37]=[C:38]([C:43]([CH3:46])([CH3:45])[CH3:44])[CH:39]=6)[C:34]5=[O:48])[C:28]=4[CH2:49][O:50][C:51](=[O:53])[CH3:52])[CH:26]=3)=[CH:18][CH:19]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[C:43]([C:38]1[CH:39]=[C:40]2[C:35](=[C:36]([F:47])[CH:37]=1)[C:34](=[O:48])[N:33]([C:29]1[CH:30]=[CH:31][CH:32]=[C:27]([C:25]3[CH:26]=[C:21]([NH:20][C:17]4[N:16]=[CH:15][C:14]([CH:11]5[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]5)=[CH:19][CH:18]=4)[C:22]4[N:23]([CH:54]=[CH:55][N:56]=4)[CH:24]=3)[C:28]=1[CH2:49][O:50][C:51](=[O:53])[CH3:52])[N:42]=[CH:41]2)([CH3:44])([CH3:45])[CH3:46]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86686849HCID 86686849, compound

Product 1

HCID 86686848HCID 86686848, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To the solution of 6-{6-[2-acetoxymethyl-3-(6-tert-butyl-8-fluoro-1-oxo-1H-phthalazin-2-yl)phenyl]-imidazo[1,2-a]pyridin-8-ylamino}-3′,4′,5′,6′-tetrahydro-2′H-[3,4′]bipyridinyl-1′-carboxylic acid tert-butyl ester (280 mg, 0.3689 mmol) in DCM (8 mL) was added TFA (1.4 mL) and the solution was stirred at room temperature for one hour. TLC showed a complete reaction. The solution was poured onto water and extracted with ethyl acetate. The combined organic layers were washed with brine, dried over Na2SO4, and concentrated to give the crude product used directly to the next step (260 mg). LC-MS: 660 [M+1]+, tR=1.270 min.

Workup

  1. customa complete reaction
  2. additionThe solution was poured onto water
  3. extractionextracted with ethyl acetate
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-20c7f7e1fa7146b6ae125abc633554d8
Source dataset
uspto-grants-2014_06
Patent number
US08742098B2

Reaction notes

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