Methylamine → HCID 68832183, compound

HRID 490567Notes

Reaction equation

HRID 490567 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[N:9]([CH2:13][C:14]([OH:16])=O)[NH:8][C:7]2=[O:17])([O-:3])=[O:2].[CH3:18][N:19](C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.CN>CN(C=O)C>[CH3:18][NH:19][C:14](=[O:16])[CH2:13][N:9]1[C:10]2[C:6](=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:12][CH:11]=2)[C:7](=[O:17])[NH:8]1

Participants

5

Reactant 3

HCID 6329MethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 68834593HCID 68834593, compound

Product 1

HCID 68832183HCID 68832183, compoundYield 27.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of crude (5-nitro-3-oxo-2,3-dihydro-indazol-1-yl)-acetic acid (0.14 g) in DMF, was added TBTU (0.20 g), followed by N,N-ethyldiisopropylamine (0.40 mL) and after 10 minutes methylamine (0.32 mL of a 2 M solution) was added. The reaction was stirred overnight and was quenched with 2N HCl (aq.) and extracted with EtOAc. The combined organic layers were washed with brine, dried over sodium sulfate, filtered and evaporated. Flash column chromatography of the residue over silica gel afforded the desired N-methyl-2-(5-nitro-3-oxo-2,3-dihydro-indazol-1-yl)-acetamide (0.040 g) as a yellow solid. MS (ESI−):249.1 ([M−H]−).

Workup

  1. customwas quenched with 2N HCl (aq.)
  2. extractionextracted with EtOAc
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-f7584a4eb44f43c5959d32f4da096e3c
Source dataset
uspto-grants-2009_05
Patent number
US07528158B2

Reaction notes

Loading…