Hydrochloric Acid → Formic acid 2-{[(2R,6S)-2,6-dimethyl-4-morpholinyl]methyl}-N-[6-(1H-pyrazolo[3,4-b]pyridin-5-yl)-1H-indazol-4-yl]-1,3-thiazole-4-carboxamide

HRID 244758Notes

Reaction equation

HRID 244758 reaction equation
[CH3:1][C@H:2]1[O:7][C@@H:6]([CH3:8])[CH2:5][N:4]([CH2:9][C:10]2[S:11][CH:12]=[C:13]([C:15]([NH:17][C:18]3[CH:26]=[C:25]([C:27]4[CH:28]=[C:29]5[CH:35]=[N:34][N:33](S(C6C=CC=CC=6)(=O)=O)[C:30]5=[N:31][CH:32]=4)[CH:24]=[C:23]4[C:19]=3[CH:20]=[N:21][N:22]4S(C3C=CC=CC=3)(=O)=O)=[O:16])[N:14]=2)[CH2:3]1.[OH-:54].[Na+].Cl>C(O)(C)C>[CH:15]([OH:16])=[O:54].[CH3:8][C@H:6]1[O:7][C@@H:2]([CH3:1])[CH2:3][N:4]([CH2:9][C:10]2[S:11][CH:12]=[C:13]([C:15]([NH:17][C:18]3[CH:26]=[C:25]([C:27]4[CH:28]=[C:29]5[CH:35]=[N:34][NH:33][C:30]5=[N:31][CH:32]=4)[CH:24]=[C:23]4[C:19]=3[CH:20]=[N:21][NH:22]4)=[O:16])[N:14]=2)[CH2:5]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 583564282-{[(2R,6S)-2,6-Dimethyl-4-morpholinyl]methyl}-N-{1-(phenylsulfonyl)-6-[1-(phenylsulfonyl)-1H-pyrazolo[3,4-b]pyridin-5-yl]-1H-indazol-4-yl}-1,3-thiazole-4-carboxamide

Product 1

HCID 67320001Formic acid 2-{[(2R,6S)-2,6-dimethyl-4-morpholinyl]methyl}-N-[6-(1H-pyrazolo[3,4-b]pyridin-5-yl)-1H-indazol-4-yl]-1,3-thiazole-4-carboxamideYield 52.2%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

2-{[(2R,6S)-2,6-Dimethyl-4-morpholinyl]methyl}-N-{1-(phenylsulfonyl)-6-[1-(phenylsulfonyl)-1H-pyrazolo[3,4-b]pyridin-5-yl]-1H-indazol-4-yl}-1,3-thiazole-4-carboxamide (99 mg, 0.129 mmol) was suspended in Isopropanol (1 mL) and Sodium hydroxide (1 ml, 2.0 mmol) was added. The mixture was stirred at room temperature for 18 h then neutralised with 2 M HCl (aq.) and the solvent was removed under a stream of nitrogen. The residue was dissolved in DMSO (2 ml) (insoluble salt was filtered off through a filter tube) and the samples (2×1 ml injections) were purified by mass directed autoprep HPLC (Method F). The product-containing fractions were concentrated under a stream of nitrogen to give the title compound as a white solid (18 mg).

Workup

  1. customthe solvent was removed under a stream of nitrogen
  2. dissolutionThe residue was dissolved in DMSO (2 ml) (insoluble salt was filtered off through a filter tube)
  3. customthe samples (2×1 ml injections) were purified by mass
  4. concentrationThe product-containing fractions were concentrated under a stream of nitrogen

Sources & evidence

ORD record
ord-7099b91722a44122a5ea5f3073faafb7
Source dataset
uspto-grants-2014_02
Patent number
US08658635B2

Reaction notes

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