Water → HCID 90411799, compound

HRID 2175957Notes

Reaction equation

HRID 2175957 reaction equation
Cl.[CH:2]12[NH:8][CH:5]([CH2:6][CH2:7]1)[CH2:4][CH:3]2[CH2:9][OH:10].[CH3:11][C:12]1[CH:13]=[CH:14][C:15]([N:21]2[N:25]=[CH:24][CH:23]=[N:22]2)=[C:16]([CH:20]=1)[C:17](O)=[O:18].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.O>CN(C=O)C>[NH3:8].[CH3:9][OH:10].[OH:10][CH2:9][CH:3]1[CH2:4][CH:5]2[N:8]([C:17]([C:16]3[CH:20]=[C:12]([CH3:11])[CH:13]=[CH:14][C:15]=3[N:21]3[N:25]=[CH:24][CH:23]=[N:22]3)=[O:18])[CH:2]1[CH2:7][CH2:6]2

Participants

7

Reactant 4

HCID 962WaterHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 532601655-methyl-2-(2H-1,2,3-triazol-2-yl)benzoic acidHCID 90412474HCID 90412474, compound

Product 2

HCID 21705897Ammonia methanolYield 1%HCID 90411799HCID 90411799, compoundYield 46%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To the title compound of Step A in DMF was added TEA, 5-methyl-2-(2H-1,2,3-triazol-2-yl)benzoic acid and HATU. After 18 h, H2O was added and the mix extracted with EtOAc (2×). The combined organics were washed with brine and dried (Na2SO4). Silica gel chromatography (1-7% 2M NH3/MeOH in DCM) gave the title compound (371 mg, 46%). MS (ESI) mass calcd. for C17H20N4O2, 312.2; m/z found 313.2 [M+H]+.

Workup

  1. extractionthe mix extracted with EtOAc (2×)
  2. washThe combined organics were washed with brine
  3. dry with materialdried (Na2SO4)

Sources & evidence

ORD record
ord-ce5ac13fa3fa494d9cd047bd83dad735
Source dataset
uspto-grants-2015_06
Patent number
US09062078B2

Reaction notes

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