Trifluoroacetic acid methylene chloride → N-[6-amino-2-(2-phenylethynyl)pyridin-3-yl]oxane-4-carboxamide

HRID 535398Notes

Reaction equation

HRID 535398 reaction equation
C(OC(=O)[NH:7][C:8]1[CH:13]=[CH:12][C:11]([NH:14][C:15]([CH:17]2[CH2:22][CH2:21][O:20][CH2:19][CH2:18]2)=[O:16])=[C:10]([C:23]#[C:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[N:9]=1)(C)(C)C.C(Cl)Cl.C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH2:7][C:8]1[N:9]=[C:10]([C:23]#[C:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[C:11]([NH:14][C:15]([CH:17]2[CH2:22][CH2:21][O:20][CH2:19][CH2:18]2)=[O:16])=[CH:12][CH:13]=1

Participants

4

Reactant 2

HCID 21863450Trifluoroacetic acid methylene chlorideHCID 86694378tert-butyl-N-[5-(oxane-4-carbonylamino)-6-(2-phenylethynyl)pyridin-2-yl]-carbamate

Product 1

HCID 86694381N-[6-amino-2-(2-phenylethynyl)pyridin-3-yl]oxane-4-carboxamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of tert-butyl-N-[5-(oxane-4-carbonylamino)-6-(2-phenylethynyl)pyridin-2-yl]-carbamate C5b (29 mg, 0.07 mmol) and DCM:TFA (9:1, 3 ml) is stirred at RT for 2 h. The mixture is diluted with DCM and extracted with a saturated aqueous solution of NaHCO3.

Workup

  1. extractionextracted with a saturated aqueous solution of NaHCO3

Sources & evidence

ORD record
ord-5d3d5202a1ba4bc08e031798e087f841
Source dataset
uspto-grants-2014_10
Patent number
US08859541B2

Reaction notes

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