Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1) → HCID 67169913, compound

HRID 1918322Notes

Reaction equation

HRID 1918322 reaction equation
F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2N=CC=CC=2N=N1.[CH3:25][O:26][C:27]([C:29]1([NH2:36])[CH2:34][CH:33]2[O:35][CH:30]1[CH2:31][CH2:32]2)=[O:28].[CH3:37][O:38][C:39]1[CH:47]=[CH:46][C:42]([C:43](O)=[O:44])=[CH:41][C:40]=1[O:48][CH2:49][CH2:50][C:51]1[CH:52]=[C:53]([CH3:57])[CH:54]=[CH:55][CH:56]=1>CN(C=O)C.CC(=O)OCC>[CH3:25][O:26][C:27]([C:29]1([NH:36][C:43](=[O:44])[C:42]2[CH:46]=[CH:47][C:39]([O:38][CH3:37])=[C:40]([O:48][CH2:49][CH2:50][C:51]3[CH:52]=[C:53]([CH3:57])[CH:54]=[CH:55][CH:56]=3)[CH:41]=2)[CH2:34][CH:33]2[O:35][CH:30]1[CH2:31][CH2:32]2)=[O:28]

Participants

6

Reactant 3

HCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 67076259HCID 67076259, compoundHCID 67170305HCID 67170305, compound

Product 1

HCID 67169913HCID 67169913, compoundYield 100.1%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

550 mg of O-(7-azabenzotriazol-1-yl)-1,1,3,3-tetramethyluronium hexafluorophosphate (HATU), 300 mg of 2-amino-7-oxa-bicyclo[2.2.1]heptane-2-carboxylic acid methyl ester and 410 mg of 4-methoxy-3-(2-m-tolyl-ethoxy)-benzoic acid (example 2) were stirred in 20 ml of anhydrous DMF for 15 h at room temperature. The mixture was diluted with 150 ml of EA and washed three times with 50 ml each of a saturated aqueous sodium carbonate solution and then three times with 50 ml each of a 10% aqueous sodium hydrogensulfate solution. The organic layer was dried with magnesium sulfate, evaporated to dryness and the residue purified by silica gel chromatography (HEP/EA gradient) to yield 630 mg of the title compound as a racemic mixture.

Workup

  1. washwashed three times with 50 ml each of a saturated aqueous sodium carbonate solution
  2. dry with materialThe organic layer was dried with magnesium sulfate
  3. customevaporated to dryness
  4. customthe residue purified by silica gel chromatography (HEP/EA gradient)

Sources & evidence

ORD record
ord-7acebb503c8343cebc18b684092b62d1
Source dataset
uspto-grants-2013_12
Patent number
US08618304B2

Reaction notes

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