HCID 117666121, compound → N1-((3-(4-isopropoxyphenyl)-1-methyl-1H-pyrazol-4-yl)methyl)-N1,N2-dimethylethane-1,2-diamine

HRID 526773Notes

Reaction equation

HRID 526773 reaction equation
[CH2:1]([N:8](C)[CH2:9][CH2:10][N:11]([CH2:13][C:14]1[C:15]([C:20]2[CH:25]=[CH:24][C:23]([O:26][CH:27]([CH3:29])[CH3:28])=[CH:22][CH:21]=2)=[N:16][N:17]([CH3:19])[CH:18]=1)[CH3:12])C1C=CC=CC=1>CO.[Pd]>[CH:27]([O:26][C:23]1[CH:22]=[CH:21][C:20]([C:15]2[C:14]([CH2:13][N:11]([CH3:12])[CH2:10][CH2:9][NH:8][CH3:1])=[CH:18][N:17]([CH3:19])[N:16]=2)=[CH:25][CH:24]=1)([CH3:29])[CH3:28]

Participants

4

Reactant 1

HCID 117666121HCID 117666121, compound

Product 1

HCID 117665977N1-((3-(4-isopropoxyphenyl)-1-methyl-1H-pyrazol-4-yl)methyl)-N1,N2-dimethylethane-1,2-diamineYield 59%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a suspension of N1-benzyl-N2-((3-(4-isopropoxyphenyl)-1-methyl-1H-pyrazol-4-yl)methyl)-N1,N2-dimethylethane-1,2-diamine (62 mg, 0.15 mmol) and Pd/C (10 mg) in methanol was purged H2 gas for 2 h. The resulting mixture was filtered through celite and washed with methanol (5 mL×2). The combined filtrate was concentrated to afford N1-((3-(4-isopropoxyphenyl)-1-methyl-1H-pyrazol-4-yl)methyl)-N1,N2-dimethylethane-1,2-diamine (28 mg, 58%). 1H NMR (400 MHz, DMSO-d6): δ 8.12 (s, 1H), 7.48 (d, J=8.4 Hz, 2H), 6.98 (d, J=8.8 Hz, 2H), 4.71-4.61 (m, 1H), 4.44-4.27 (m, 2H), 3.90 (s, 3H), 3.50-3.18 (m, 5H), 3.11-3.04 (m, 1H), 2.65-2.45 (m, 4H) 1.29 (d, J=6 Hz, 6H) ppm. LCMS (method C): RT=1.76 min, m/z=317.3 [M+H]+.

Workup

  1. customwas purged H2 gas for 2 h
  2. filtrationThe resulting mixture was filtered through celite
  3. washwashed with methanol (5 mL×2)
  4. concentrationThe combined filtrate was concentrated

Sources & evidence

ORD record
ord-5275ff9c701341c189e09df31f3df79d
Source dataset
uspto-grants-2016_05
Patent number
US09346761B2

Reaction notes

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