Methylamine → HCID 23577857, compound

HRID 1827455Notes

Reaction equation

HRID 1827455 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[NH:11][C:12]1[CH:20]=[C:19]2[C:15]([C:16]([C:27]([OH:29])=O)=[N:17][N:18]2[CH:21]2[CH2:26][CH2:25][CH2:24][CH2:23][O:22]2)=[CH:14][CH:13]=1)=[O:4].[CH2:30]([N:32](CC)CC)C.CN.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C>[CH3:1][O:2][C:3](=[O:4])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[NH:11][C:12]1[CH:20]=[C:19]2[C:15]([C:16]([C:27](=[O:29])[NH:32][CH3:30])=[N:17][N:18]2[CH:21]2[CH2:26][CH2:25][CH2:24][CH2:23][O:22]2)=[CH:14][CH:13]=1

Participants

6

Reactant 4

HCID 6329MethylamineHCID 8471TriethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 22136534HCID 22136534, compound

Product 1

HCID 23577857HCID 23577857, compoundYield 42%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 6-(2-Methoxycarbonyl-phenylamino)-1-(tetrahydro-pyran-2-yl)-1H-indazole-3-carboxylic acid (0.50 g, 1.27 mmol) in DMF was added triethylamine (0.42 mL, 3.04 mmol), methylamine (1.9 mL, 3.81 mmol), and HATU (0.578 g, 1.52 mmol). The reaction was stirred for 3 hours and then concentrated by rotary evaporation. The crude oil was chromatographed (50 g silica gel, 25–50% EtOAc/hexanes) to yield the desired product (214 mg, 42%).

Workup

  1. concentrationconcentrated by rotary evaporation
  2. customThe crude oil was chromatographed (50 g silica gel, 25–50% EtOAc/hexanes)

Sources & evidence

ORD record
ord-114204fc88f04b03bb18e56ff67060fe
Source dataset
uspto-grants-2006_05
Patent number
US07053107B2

Reaction notes

Loading…