Ammonia → HCID 86685984, compound

HRID 2277688Notes

Reaction equation

HRID 2277688 reaction equation
C[N:2](C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(CC)CC.N.[Cl:33][C:34]1[CH:35]=[C:36]2[C:41](=[CH:42][CH:43]=1)[C:40](=[O:44])[N:39]([C:45]1[CH:46]=[C:47]([O:51][CH2:52][C:53](O)=[O:54])[CH:48]=[N:49][CH:50]=1)[CH2:38][CH2:37]2>CN(C=O)C.O>[Cl:33][C:34]1[CH:35]=[C:36]2[C:41](=[CH:42][CH:43]=1)[C:40](=[O:44])[N:39]([C:45]1[CH:46]=[C:47]([O:51][CH2:52][C:53]([NH2:2])=[O:54])[CH:48]=[N:49][CH:50]=1)[CH2:38][CH2:37]2

Participants

7

Reactant 4

HCID 222AmmoniaHCID 8471TriethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 86685985HCID 86685985, compound

Product 1

HCID 86685984HCID 86685984, compoundYield 16.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

HATU (38 mg, 0.1 mmol), Et3N (10.1 mg, 0.1 mmol) and ammonia (1.6 M in 1,4-dioxane, 125 μL, 0.2 mmol) were added to a solution of [5-(6-chloro-1-oxo-3,4-dihydro-1H-isoquinolin-2-yl)-pyridin-3-yloxy]-acetic acid (33.2 mg, 0.1 mmol) in DMF (2 mL). The reaction mixture was stirred at RT overnight before it was poured into water and extracted with EtOAc (2×5 mL). The organic layers were dried over anhy. Na2SO4, filtered and concentrated in vacuo to give a crude product which was purified by prep-HPLC to give title compound (5.4 mg, 16%) as a white solid. MS: 332.1 (M+H+).

Workup

  1. extractionextracted with EtOAc (2×5 mL)
  2. customThe organic layers were dried over anhy
  3. filtrationNa2SO4, filtered
  4. concentrationconcentrated in vacuo
  5. customto give a crude product which
  6. customwas purified by prep-HPLC

Sources & evidence

ORD record
ord-b4daf1770136426cb9d61ad01eff48e8
Source dataset
uspto-grants-2015_09
Patent number
US09133158B2

Reaction notes

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