Cesium carbonate → HCID 67515706, compound

HRID 919640Notes

Reaction equation

HRID 919640 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH2:11][CH:10]([NH:14][C:15]2[C:20]([C:21]([O:23][CH3:24])=[O:22])=[CH:19][N:18]=[C:17]3[N:25](S(C4C=CC(C)=CC=4)(=O)=O)[CH:26]=[CH:27][C:16]=23)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C([O-])([O-])=O.[Cs+].[Cs+].[OH-].[Na+]>C1COCC1.CO>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH2:11][CH:10]([NH:14][C:15]2[C:20]([C:21]([O:23][CH3:24])=[O:22])=[CH:19][N:18]=[C:17]3[NH:25][CH:26]=[CH:27][C:16]=23)[CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 14798Sodium HydroxideHCID 67517143HCID 67517143, compound

Product 1

HCID 67515706HCID 67515706, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

A mixture of methyl 4-((1-(tert-butoxycarbonyl)piperidin-3-yl)amino)-1-tosyl-1H-pyrrolo[2,3-b]pyridine-5-carboxylate (667 mg, 1.26 mmol, 1.0 eq) and Cs2CO3 (824 mg, 2.52 mmol) in THF/MeOH (1:1, 5 mL) was stirred at rt for 16 h. The solvent was removed in vacuo and the residue suspended in H2O/MeOH (1:1, 5 mL) and treated with NaOH (77 mg, 1.92 mmol, 2 eq) and then heated to 80° C. for 16. The solvent was reduced in vacuo and adjusted to pH 4-5. The precipitate was filtered to give the title compound (263 mg, yield: 76%) as a brown solid which was used without further purification. ESI-MS (M+H) 361.18.

Workup

  1. customThe solvent was removed in vacuo
  2. temperatureheated to 80° C. for 16
  3. filtrationThe precipitate was filtered

Sources & evidence

ORD record
ord-7e3f6273c3704bbe91219c5ccbbe4c9c
Source dataset
uspto-grants-2016_03
Patent number
US09273028B2

Reaction notes

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