Sodium Bicarbonate → HCID 136408067, compound

HRID 2205766Notes

Reaction equation

HRID 2205766 reaction equation
[Cl:1][C:2]1[C:7]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[N:6][N:5]=[C:4]2[N:14]([CH2:33][CH2:34][N:35]3[CH2:40][CH2:39][N:38]([CH3:41])[CH2:37][CH2:36]3)[N:15]=[C:16]([C:17]3[N:18](C(OC(C)(C)C)=O)[C:19]4[C:24]([CH:25]=3)=[CH:23][CH:22]=[CH:21][CH:20]=4)[C:3]=12.C([O-])(O)=O.[Na+]>C(Cl)Cl.FC(F)(F)C(O)=O>[Cl:1][C:2]1[C:7]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[N:6][N:5]=[C:4]2[N:14]([CH2:33][CH2:34][N:35]3[CH2:40][CH2:39][N:38]([CH3:41])[CH2:37][CH2:36]3)[N:15]=[C:16]([C:17]3[NH:18][C:19]4[C:24]([CH:25]=3)=[CH:23][CH:22]=[CH:21][CH:20]=4)[C:3]=12

Participants

5

Reactant 2

HCID 516892Sodium Bicarbonate2×HCID 86717266HCID 86717266, compound

Product 1

HCID 136408067HCID 136408067, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of tert-butyl 2-(4-chloro-1-(2-(4-methylpiperazin-1-yl)ethyl)-5-phenyl-1H-pyrazolo[3,4-c]pyridazin-3-yl)-1H-indole-1-carboxylate (29 mg, 0.051 mmol) in CH2Cl2 (3 mL) and trifluoroacetic acid (0.8 mL) was stirred at room temperature for 1 d. Solid NaHCO3 was added until no gas was evolved and sat. aq. NaHCO3 solution and CH2Cl2 was added. The layers were separated and the aqueous was extracted with CH2Cl2, the combined organics were dried (MgSO4), filtered and concentrated in vacuo. The residue was freeze dried from acetonitrile and water to provide Compound Im as a solid.

Workup

  1. customThe layers were separated
  2. extractionthe aqueous was extracted with CH2Cl2
  3. dry with materialthe combined organics were dried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. dry with materialdried from acetonitrile and water
  7. customto provide Compound Im as a solid

Sources & evidence

ORD record
ord-544030ced0844cd59b7ad787dd523986
Source dataset
uspto-grants-2016_06
Patent number
US09371332B2

Reaction notes

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