Hydrochloric Acid → HCID 59304361, compound

HRID 2241401Notes

Reaction equation

HRID 2241401 reaction equation
FC(F)(F)C([O:5][CH:6]1[CH2:11][CH2:10][CH2:9][CH:8]([NH:12][C:13]2[C:21]3[C:16](=[N:17][CH:18]=[CH:19][C:20]=3[O:22][C:23]3[CH:28]=[CH:27][C:26]([NH:29][C:30]([C:32]4[C:37](=[O:38])[N:36]([C:39]5[CH:44]=[CH:43][C:42]([F:45])=[CH:41][CH:40]=5)[N:35]=[CH:34][CH:33]=4)=[O:31])=[CH:25][C:24]=3[F:46])[NH:15][N:14]=2)[CH2:7]1)=O.Cl.CCOC(C)=O>[Li+].[OH-].C1COCC1.CO>[F:46][C:24]1[CH:25]=[C:26]([NH:29][C:30]([C:32]2[C:37](=[O:38])[N:36]([C:39]3[CH:40]=[CH:41][C:42]([F:45])=[CH:43][CH:44]=3)[N:35]=[CH:34][CH:33]=2)=[O:31])[CH:27]=[CH:28][C:23]=1[O:22][C:20]1[CH:19]=[CH:18][N:17]=[C:16]2[NH:15][N:14]=[C:13]([NH:12][CH:8]3[CH2:9][CH2:10][CH2:11][CH:6]([OH:5])[CH2:7]3)[C:21]=12

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 59304269HCID 59304269, compound

Product 1

HCID 59304361HCID 59304361, compoundYield 29.1%

Reagents, catalysts & solvents 3

HCID 3939Lithium HydroxideCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

LiOH (2M solution, 2 drops) was added into a solution of 3-(4-(2-fluoro-4-(1-(4-fluorophenyl)-6-oxo-1,6-dihydropyridazine-5-carboxamido)phenoxy)-1H-pyrazolo[3,4-b]pyridin-3-ylamino)cyclohexyl 2,2,2-trifluoroacetate (10 mg, 0.015 mmol, obtained from Example 131, Step C) in THF (0.5 mL) and MeOH (0.1 mL). HCl (5M, 0.1 mL). EtOAc was added to dilute the reaction mixture. The organic layer was separated, washed with brine, dried with Na2SO4, filtered and concentrated to afford the product (2.5 mg, 29% yield) as a yellow solid. LRMS (APCI pos) m/e 574.2 (M+H). 1H NMR (DMSO-d6, 400 MHz): δ 8.38 (d, 1H), 8.26 (d, 1H), 8.12 (d, 1H), 8.05 (dd, 1H), 7.66-7.70 (m, 2H), 7.56-7.62 (m, 1H), 7.48-7.54 (m, 1H), 7.38-7.44 (m, 2H), 6.80-7.00 (m, 1H), 6.00-6.05 (m, 1H), 3.80-4.00 (m, 2H), 3.50-3.80 (m, 1H), 1.80-2.00 (m, 1H), 1.60-1.80 (m, 2H), 1.40-1.60 (m, 1H), 1.10-1.30 (m, 2H), 0.80-0.90 (m, 2H).

Workup

  1. additionto dilute the reaction mixture
  2. customThe organic layer was separated
  3. washwashed with brine
  4. dry with materialdried with Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-7190154b9c224c2784074cbf3e8c9d42
Source dataset
uspto-grants-2010_05
Patent number
US07723330B2

Reaction notes

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