Methylamine → 4-{2-[(1-Methylcarbamoyl-cyclohexylmethyl)-amino]-benzooxazol-6-yloxy}-pyridine-2-carboxylic acid methylamide

HRID 1922204Notes

Reaction equation

HRID 1922204 reaction equation
[CH3:1][NH:2][C:3]([C:5]1[CH:10]=[C:9]([O:11][C:12]2[CH:31]=[CH:30][C:15]3[N:16]=[C:17]([NH:19][CH2:20][C:21]4([C:27](O)=[O:28])[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]4)[O:18][C:14]=3[CH:13]=2)[CH:8]=[CH:7][N:6]=1)=[O:4].C[CH2:33][N:34](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.C1COCC1>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:31]=[CH:30][C:15]3[N:16]=[C:17]([NH:19][CH2:20][C:21]4([C:27](=[O:28])[NH:34][CH3:33])[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26]4)[O:18][C:14]=3[CH:13]=2)[CH:8]=[CH:7][N:6]=1)=[O:4]

Participants

8

Reactant 5

HCID 6329MethylamineHCID 8028TetrahydrofuranHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 248213051-{[6-(2-Methylcarbamoyl-pyridin-4-yloxy)-benzooxazol-2-ylamino]-methyl}-cyclohexanecarboxylic acid

Product 1

HCID 577254944-{2-[(1-Methylcarbamoyl-cyclohexylmethyl)-amino]-benzooxazol-6-yloxy}-pyridine-2-carboxylic acid methylamide

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 1-{[6-(2-methylcarbamoyl-pyridin-4-yloxy)-benzooxazol-2-ylamino]-methyl}-cyclohexanecarboxylic acid (1 eq) in DMF was added DIPEA (3 eq) and [dimethylamino-([1,2,3]triazolo[4,5-b]pyridin-3-yloxy)-methylene]-dimethyl-ammonium hexafluoro phosphate (1 eq). This was stirred at room temperature for 2 hours, then a 2 M solution of methylamine in THF (5 eq) was added and allowed to react overnight at 70° C. The mixture was diluted with ethyl acetate and washed twice with a saturated aqueous solution of ammonium chloride and once with brine, then dried with anhydrous sodium sulfate, filtered and concentrated, then purified by preparatory reverse phase HPLC. MH+=438.1.

Workup

  1. customto react overnight at 70° C
  2. washwashed twice with a saturated aqueous solution of ammonium chloride and once with brine
  3. dry with materialdried with anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. custompurified by preparatory reverse phase HPLC

Sources & evidence

ORD record
ord-c673303e2717402b9a5ca0bb99cc6bbe
Source dataset
uspto-grants-2012_05
Patent number
US08173689B2

Reaction notes

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