Ammonium Bicarbonate → HCID 178513483, compound

HRID 1754572Notes

Reaction equation

HRID 1754572 reaction equation
[O:1]=[C:2]1[C:11]2=[CH:12][NH:13][N:14]=[C:10]2[C:9]2[CH:8]=[C:7]([C:15](O)=[O:16])[C:6]([C:18]3[CH:23]=[CH:22][N:21]=[CH:20][CH:19]=3)=[CH:5][C:4]=2[N:3]1[CH2:24][C:25]([F:28])([F:27])[F:26].C(=O)(O)[O-].[NH4+:33].C(OC(OC(C)(C)C)=O)(OC(C)(C)C)=O>N1C=CC=CC=1.CCOC(C)=O>[O:1]=[C:2]1[C:11]2=[CH:12][NH:13][N:14]=[C:10]2[C:9]2[CH:8]=[C:7]([C:15]([NH2:33])=[O:16])[C:6]([C:18]3[CH:19]=[CH:20][N:21]=[CH:22][CH:23]=3)=[CH:5][C:4]=2[N:3]1[CH2:24][C:25]([F:27])([F:26])[F:28]

Participants

5

Reactant 3

HCID 14013Ammonium BicarbonateHCID 90495Di-tert-butyl dicarbonateHCID 178524020HCID 178524020, compound

Product 1

HCID 178513483HCID 178513483, compoundYield 7.9%

Reagents, catalysts & solvents 1

HCID 21992828Pyridine ethyl acetateSolvent

Procedure

A mixture of 4-oxo-7-(pyrid-4-yl)-5-(2,2,2-trifluoroethyl)-4,5-dihydro-2H-pyrazolo[4,3-c]quinoline-8-carboxylic acid [Example 11] (38 mg, 010 mmol), ammonium bicarbonate (46 mg, 0.59 mmol) and di-tert-butyl dicarbonate (47 mg, 0.22 mmol) in 1 mL of pyridine/EtOAc (1/1) is stirred at room temperature under nitrogen for 16 hours and then concentrated to dryness. After purification by preparative HPLC on a C18 reverse phase [eluent A: H2O/0.1M CH3COONH4 (90/10); eluent B: CH3CN/0.1M CH3COONH4 (90/10); gradient A/B: 95/5 to 50/50], 3 mg of a white powder are obtained (8%).

Workup

  1. concentrationconcentrated to dryness
  2. customAfter purification by preparative HPLC on a C18 reverse phase [eluent A

Sources & evidence

ORD record
ord-a81f5e868501468f8974016d0681734e
Source dataset
uspto-grants-2015_10
Patent number
US09169246B2

Reaction notes

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