Potassium Carbonate → N-((4S)-2-amino-7'-methoxyspiro[1,3-oxazole-4,9'-xanthen]-2'-yl)-5-chloro-2-pyridinecarboxamide

HRID 1970312Notes

Reaction equation

HRID 1970312 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]([NH:10][C:11]2[CH:24]=[C:23]3[C:14]([O:15][C:16]4[CH:17]=[CH:18][C:19]([O:36][CH3:37])=[CH:20][C:21]=4[C@@:22]43[CH2:28][O:27][C:26]([NH:29]C(=O)C(F)(F)F)=[N:25]4)=[CH:13][CH:12]=2)=[O:9])=[N:6][CH:7]=1.C(=O)([O-])[O-].[K+].[K+]>CO>[NH2:29][C:26]1[O:27][CH2:28][C@:22]2([N:25]=1)[C:23]1[CH:24]=[C:11]([NH:10][C:8]([C:5]3[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][N:6]=3)=[O:9])[CH:12]=[CH:13][C:14]=1[O:15][C:16]1[C:21]2=[CH:20][C:19]([O:36][CH3:37])=[CH:18][CH:17]=1

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 86640719(S)-5-chloro-N-(2'-methoxy-2-(2,2,2-trifluoroacetamido)-5H-spiro[oxazole-4,9'-xanthene]-7'-yl)picolinamide

Product 1

HCID 59272386N-((4S)-2-amino-7'-methoxyspiro[1,3-oxazole-4,9'-xanthen]-2'-yl)-5-chloro-2-pyridinecarboxamide

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

A solution of (S)-5-chloro-N-(2′-methoxy-2-(2,2,2-trifluoroacetamido)-5H-spiro[oxazole-4,9′-xanthene]-7′-yl)picolinamide (0.054 g, 0.101 mmol) in methanol (3.5 mL) was treated with potassium carbonate anhydrous (0.045 g, 0.326 mmol) and stirred at RT for 30 minutes. The catalyst was removed by filtration and the filtrate was concentrated to yield the crude product as a yellowish gummy solid. The crude product was purified by preparative HPLC [gradient 10-90% MeCN (0.1% TFA)/H2O (0.1% TFA)] to give pure product which was dissolved in methanol (5 mL) and neutralized by passing the solution through a Polymer Lab-HCO3 macroporous resin cartridge, and the filtrate was concentrated to give N-((4S)-2-amino-7′-methoxyspiro[1,3-oxazole-4,9′-xanthen]-2′-yl)-5-chloro-2-pyridinecarboxamide as an off-white solid. MS (ESI pos. ion) m/z: 437 (M+1).

Workup

  1. customThe catalyst was removed by filtration
  2. concentrationthe filtrate was concentrated
  3. customto yield the crude product as a yellowish gummy solid
  4. customThe crude product was purified by preparative HPLC [gradient 10-90% MeCN (0.1% TFA)/H2O (0.1% TFA)]
  5. customto give pure product which
  6. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-ddcf89c2e6c34245a9ef6429e2127b6e
Source dataset
uspto-grants-2013_04
Patent number
US08426447B2

Reaction notes

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