2,3-Dihydro-1,4-benzodioxin-5-carboxylic acid → HCID 57725495, compound

HRID 1922209Notes

Reaction equation

[CH3:1][NH:2][C:3]([C:5]1[CH:10]=[C:9]([O:11][C:12]2[CH:21]=[CH:20][C:15]3[N:16]=[C:17]([NH2:19])[O:18][C:14]=3[CH:13]=2)[CH:8]=[CH:7][N:6]=1)=[O:4].[CH2:22]1[O:31][C:30]2[C:25](=[C:26]([C:32](O)=[O:33])[CH:27]=[CH:28][CH:29]=2)[O:24][CH2:23]1.CCN(C(C)C)C(C)C.F[P-](F)(F)(F)(F)F.CN(C(=[N+](C)C)ON1C2=NC=CC=C2N=N1)C>CN(C=O)C.C(OCC)(=O)C>[CH3:1][NH:2][C:3]([C:5]1[CH:10]=[C:9]([O:11][C:12]2[CH:21]=[CH:20][C:15]3[N:16]=[C:17]([NH:19][C:32]([C:26]4[C:25]5[O:24][CH2:23][CH2:22][O:31][C:30]=5[CH:29]=[CH:28][CH:27]=4)=[O:33])[O:18][C:14]=3[CH:13]=2)[CH:8]=[CH:7][N:6]=1)=[O:4]

Participants

Conditions

Temperature: 40 °C

Procedure

4-(2-Amino-benzooxazol-6-yloxy)-pyridine-2-carboxylic acid methylamide (1 eq) and 2,3-dihydro-1,4-benzodioxane-5-carboxylic acid (1 eq) were dissolved in DMF. To this solution were added DIPEA (3 eq) and [dimethylamino-([1,2,3]triazolo[4,5-b]pyridin-3-yloxy)-methylene]-dimethyl-ammonium hexafluoro phosphate (1 eq). The mixture was stirred at 40° C. overnight, then diluted with ethyl acetate and washed once each with 1N HCl, saturated aqueous sodium bicarbonate, and brine, and finally dried with anhydrous sodium sulfate, filtered, and concentrated. This was purified by preparatory reverse phase HPLC. MH+=447.0.

Workup

washwashed once each with 1N HCl, saturated aqueous sodium bicarbonate, and brine
dry with materialfinally dried with anhydrous sodium sulfate
filtrationfiltered
concentrationconcentrated
customThis was purified by preparatory reverse phase HPLC

Sources & evidence

ORD record: ord-d407fa08722a44909e898fca4cb58ebf
Source dataset: uspto-grants-2012_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08173689B2

Reaction notes

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