Methylamine → HCID 70896114, compound

HRID 2403675Notes

Reaction equation

HRID 2403675 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][N:6]=[C:5]2[C:11]([OH:13])=O.CN.Cl.[CH3:17][N:18](C)CCCN=C=NCC.O.ON1C2C=CC=CC=2N=N1.CN1CCOCC1>CN(C)C=O>[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][N:6]=[C:5]2[C:11]([NH:18][CH3:17])=[O:13]

Participants

7

Reactant 5

HCID 6329MethylamineHCID 79724-MethylmorpholineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 71573585-bromo-1H-indazole-3-carboxylic Acid

Product 1

HCID 70896114HCID 70896114, compoundYield 56%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 5-bromo-1H-indazole-3-carboxylic acid (1.2 g, 5.0 mmol) in N,N-dimethylformamide (20 mL) was added methyl amine (5 mL, 2 M in tetrahydrofuran, 10 mmol), 1, (3-dimethylaminopropyl)-3-ethyl carbodiimide hydrochloride (1.4 g, 7.5 mmol), 1-hydroxybenzotriazole hydrate (1.2 g, 7.5 mmol), and N-methylmorpholine (1.0 g, 10 mmol). The reaction was stirred at room temperature overnight. The reaction was concentrated and purification by flash column chromatography gave the title compound (0.71 g, 56%) as a colorless solid. 1H NMR (400 MHz, DMSO-d6, δ): 13.8 (br. s., 1 H), 8.41 (m, 1 H), 8.31 (s, 1 H), 7.60 (d, J=8.8 Hz, 1 H), 7.51-7.54 (m, 1 H), 2.80 (d, J=4.8 Hz, 3 H).

Workup

  1. concentrationThe reaction was concentrated
  2. custompurification by flash column chromatography

Sources & evidence

ORD record
ord-31fd44a253644ccab0f07ffb0a41255d
Source dataset
uspto-grants-2014_08
Patent number
US08802688B2

Reaction notes

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