Dimethylamine → HCID 21789945, compound

HRID 2383414Notes

Reaction equation

HRID 2383414 reaction equation
[O:1]=[C:2]1[CH:10]([CH:11]=O)[CH2:9][CH2:8][C:7]2[N:6]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[N:5]=[CH:4][C:3]1=2.[CH3:19][NH:20][CH3:21]>C1(C)C=CC=CC=1.C(OCC)C.C1COCC1>[CH3:19][N:20](/[CH:11]=[C:10]1\[C:2](=[O:1])[C:3]2[CH:4]=[N:5][N:6]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[C:7]=2[CH2:8][CH2:9]\1)[CH3:21]

Participants

6

Reactant 2

HCID 674DimethylamineHCID 59490381HCID 59490381, compound

Product 1

HCID 21789945HCID 21789945, compoundYield 80%

Reagents, catalysts & solvents 3

HCID 1140TolueneSolventHCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 4-oxo-1-phenyl-4,5,6,7-tetrahydro-1H-indazole-5-carbaldehyde (1.1 g, 4.58 mol) in toluene (50 mL) and diethylether (25 mL) was added dimethylamine (3 mL, 6 mmol) as a solution in THF (10 mL). The reaction was stirred for at room temperature for 40 hours. The reaction was then concentrated under reduced pressure to give a brown residue, which was triturated with hexane to give the desired product (1 g, 80%) as a solid. 1H NMR (DMSO-d6, 400 MHz): δδ 7.91 (s, 1H), 7.59-7.53 (m, 4H), 7.45-7.42 (m, 1H), 7.36 (s, 1H), 3.07 (s, 6H), 2.95 (s, 4H); LCMS [M+H]: 267.

Workup

  1. concentrationThe reaction was then concentrated under reduced pressure
  2. customto give a brown residue, which
  3. customwas triturated with hexane

Sources & evidence

ORD record
ord-c07aab6d9d4f47e29bd3bfa86251646c
Source dataset
uspto-grants-2012_09
Patent number
US08263610B2

Reaction notes

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