Dimethylamine, hydrochloride → HCID 47162229, compound

HRID 1771402Notes

Reaction equation

HRID 1771402 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][N:8]=[C:7]2[C:13]([OH:15])=O)([O-:3])=[O:2].Cl.[CH3:17][NH:18][CH3:19].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C>CN(C=O)C.O>[CH3:17][N:18]([CH3:19])[C:13]([C:7]1[C:6]2[C:10](=[CH:11][CH:12]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=2)[NH:9][N:8]=1)=[O:15]

Participants

7

Reactant 4

HCID 10473Dimethylamine, hydrochlorideHCID 81531DiisopropylethylamineHCID 71446525-nitro-1H-indazole-3-carboxylic AcidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

Product 1

HCID 47162229HCID 47162229, compoundYield 96.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 5-nitro-1H-indazole-3-carboxylic acid (1.01 g, 4.88 mmol), dimethylamine hydrochloride (1.99 g, 24.4 mmol) and HATU (2.78 g, 7.31 mmol) in DMF at RT was added DIPEA (4.3 mL, 24 mmol) and the reaction mixture kept at RT for 18 hr and then diluted with water (150 mL). The resulting precipitate was collected by filtration and was dried in vacuo to afford N,N-dimethyl-5-nitro-1H-indazole-3-carboxamide as a pale yellow solid (1.10 g, 92%); Rt 0.26 min (Method 2, acidic); m/z 235 (M+H)+ (ES+).

Workup

  1. filtrationThe resulting precipitate was collected by filtration
  2. customwas dried in vacuo

Sources & evidence

ORD record
ord-ffdd103d212f410a8ce0780908f3af0e
Source dataset
uspto-grants-2016_02
Patent number
US09249125B2

Reaction notes

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