Isobutyryl chloride → HCID 67499511, compound

HRID 1484723Notes

Reaction equation

HRID 1484723 reaction equation
[C:1](Cl)(=[O:5])[CH:2]([CH3:4])[CH3:3].[CH3:7][NH:8][C:9]1[CH:10]=[N:11][N:12]([C:14]2[CH:15]=[N:16][CH:17]=[CH:18][CH:19]=2)[CH:13]=1>ClC(Cl)C>[CH3:7][N:8]([C:9]1[CH:10]=[N:11][N:12]([C:14]2[CH:15]=[N:16][CH:17]=[CH:18][CH:19]=2)[CH:13]=1)[C:1](=[O:5])[CH:2]([CH3:4])[CH3:3]

Participants

4

Reactant 2

HCID 62325Isobutyryl chlorideHCID 67499383HCID 67499383, compound

Product 1

HCID 67499511HCID 67499511, compoundYield 54.3%

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent3×

Procedure

A solution of isobutyryl chloride (0.138 g, 1.3 mmol) in dichloroethane (1 mL) was pipetted at a dropwise rate into an ice-cold suspension of methyl-(1-pyridin-3-yl-1H-pyrazol-4-yl)-amine (0.15 g, 0.86 mmol) in dichloroethane (5 mL), stirred for 10 minutes and then treated at a dropwise rate with a solution of 4-N,N-dimethylaminopyridine (0.11 g, 0.9 mmol) in dichloroethane (1.5 mL). The cooling bath was removed after 30 minutes, stirred under nitrogen at room temperature for 14 hours, diluted with dichloroethane (40 mL), washed with water (30 mL), brine (10 mL), dried over MgSO4 and purified by reversed phase column chromatography to give a yellowish gum (0.114 g, 54%)1H NMR (300 MHz, CDCl3) δ 9.01-8.93 (m, 1H), 8.67 (s, 0.4H), 8.61 (d, J=4.2 Hz, 0.6H), 8.54 (d, 0.4H), 8.08-8.02 (m, 1H), 7.96 (s, 0.6H), 7.80 (s, 0.4H), 7.70 (s, 0.6H), 7.47-7.37 (m, 1H), 3.49 (s, 1.2H), 3.26 (s, 2.8H), 3.06-2.98 (m, 0.4H), 2.86-2.70 (m, 0.6H), 1.25 (d, J=6.1 Hz, 2.4H), 1.09 (d, J=6.6 Hz, 3.6H). ESIMS m/z 245 ([M+1]).

Workup

  1. customThe cooling bath was removed after 30 minutes
  2. stirringstirred under nitrogen at room temperature for 14 hours
  3. additiondiluted with dichloroethane (40 mL)
  4. washwashed with water (30 mL), brine (10 mL)
  5. dry with materialdried over MgSO4
  6. custompurified by reversed phase column chromatography

Sources & evidence

ORD record
ord-55a502eef9ed45cfb189982df62a752c
Source dataset
uspto-grants-2016_08
Patent number
US09422278B2

Reaction notes

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