Hydrochloric Acid → HCID 58356338, compound

HRID 244757Notes

Reaction equation

HRID 244757 reaction equation
[N:1]1([CH2:7][C:8]2[S:9][CH:10]=[C:11]([C:13]([NH:15][C:16]3[CH:24]=[C:23]([C:25]4[CH:26]=[C:27]5[CH:33]=[N:32][N:31](S(C6C=CC=CC=6)(=O)=O)[C:28]5=[N:29][CH:30]=4)[CH:22]=[C:21]4[C:17]=3[CH:18]=[N:19][N:20]4S(C3C=CC=CC=3)(=O)=O)=[O:14])[N:12]=2)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.[OH-].[Na+].Cl>C(O)(C)C>[N:1]1([CH2:7][C:8]2[S:9][CH:10]=[C:11]([C:13]([NH:15][C:16]3[CH:24]=[C:23]([C:25]4[CH:26]=[C:27]5[CH:33]=[N:32][NH:31][C:28]5=[N:29][CH:30]=4)[CH:22]=[C:21]4[C:17]=3[CH:18]=[N:19][NH:20]4)=[O:14])[N:12]=2)[CH2:2][CH2:3][O:4][CH2:5][CH2:6]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 67320095HCID 67320095, compound

Product 1

HCID 58356338HCID 58356338, compoundYield 29.9%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

2-(4-Morpholinylmethyl)-N-{1-(phenylsulfonyl)-6-[1-(phenylsulfonyl)-1H-pyrazolo[3,4-b]pyridin-5-yl]-1H-indazol-4-yl}-1,3-thiazole-4-carboxamide (124 mg, 0.167 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. The mixture was 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 cream solid (23 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-e5a66988f76d487cb91bba0415836e0b
Source dataset
uspto-grants-2014_02
Patent number
US08658635B2

Reaction notes

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