Trifluoroacetic acid → HCID 59304269, compound

HRID 2241400Notes

Reaction equation

HRID 2241400 reaction equation
COC1C=CC(C[N:8]2[C:12]3=[N:13][CH:14]=[CH:15][C:16]([O:17][C:18]4[CH:23]=[CH:22][C:21]([NH:24][C:25]([C:27]5[C:28](=[O:40])[N:29]([C:33]6[CH:38]=[CH:37][C:36]([F:39])=[CH:35][CH:34]=6)[N:30]=[CH:31][CH:32]=5)=[O:26])=[CH:20][C:19]=4[F:41])=[C:11]3[C:10]([NH:42][CH:43]3[CH2:48][CH2:47][CH2:46][CH:45](O)[CH2:44]3)=[N:9]2)=CC=1.[C:52]([OH:58])([C:54]([F:57])([F:56])[F:55])=[O:53]>>[F:55][C:54]([F:57])([F:56])[C:52]([O:58][CH:45]1[CH2:46][CH2:47][CH2:48][CH:43]([NH:42][C:10]2[C:11]3[C:12](=[N:13][CH:14]=[CH:15][C:16]=3[O:17][C:18]3[CH:23]=[CH:22][C:21]([NH:24][C:25]([C:27]4[C:28](=[O:40])[N:29]([C:33]5[CH:34]=[CH:35][C:36]([F:39])=[CH:37][CH:38]=5)[N:30]=[CH:31][CH:32]=4)=[O:26])=[CH:20][C:19]=3[F:41])[NH:8][N:9]=2)[CH2:44]1)=[O:53]

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 68515945HCID 68515945, compound

Product 1

HCID 59304269HCID 59304269, compoundYield 78%

Procedure

A solution of N-(4-(1-(4-methoxybenzyl)-3-(3-hydroxycyclohexylamino)-1H-pyrazolo[3,4-b]pyridin-4-yloxy)-3-fluorophenyl)-2-(4-fluorophenyl)-3-oxo-2,3-dihydropyridazine-4-carboxamide (40 mg, 0.058 mmol) in TFA (1 mL) was heated to 50° C. for 1 hour. Excess TFA was evaporated and the residue was dissolved in EtOAc. The organic layer was then washed with saturated aqueous NaHCO3, brine, dried with Na2SO4, filtered and concentrated to afford the product (30 mg, 78% yield) as a yellow solid. LRMS (APCI pos) m/e 670.2 (M+H). 1H NMR (DMSO-d6, 400 MHz): δ 12.20 (d, 1H), 11.70 (s, 1H), 8.38 (d, 1H), 8.26 (d, 1H), 8.12 (dd, 1H), 8.02 (dd, 1H), 7.66-7.70 (m, 2H), 7.56-7.62 (m, 1H), 7.46-7.52 (m, 1H), 7.38-7.44 (m, 2H), 6.02 (d, 2H), 5.20-5.40 (m, 1H), 3.60-3.80 (m, 1H), 2.20-2.30 (m, 1H), 2.00-2.10 (m, 2H), 1.80-1.90 (m, 2H), 1.60-1.80 (m, 2H), 1.30-1.45 (m, 1H).

Workup

  1. customExcess TFA was evaporated
  2. dissolutionthe residue was dissolved in EtOAc
  3. washThe organic layer was then washed with saturated aqueous NaHCO3, brine
  4. dry with materialdried with Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-8bc0256ba44e44d0a162443b733d1877
Source dataset
uspto-grants-2010_05
Patent number
US07723330B2

Reaction notes

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