Isobutyl chloroformate → HCID 118023801, compound

HRID 929291Notes

Reaction equation

HRID 929291 reaction equation
[CH3:1][N:2]([CH3:10])[C:3](=[O:9])[CH2:4][CH2:5][C:6]([OH:8])=O.C[CH2:12][N:13](C(C)C)[CH:14](C)C.ClC(OCC(C)C)=O.CNC1[C:31]([CH3:41])=[N:32][N:33]([C:35]2[CH:36]=[N:37][CH:38]=[CH:39][CH:40]=2)[CH:34]=1>C(Cl)Cl>[CH3:12][N:13]([CH3:14])[C:6](=[O:8])[CH2:5][CH2:4][C:3]([N:2]([CH3:10])[C:1]1[C:31]([CH3:41])=[N:32][N:33]([C:35]2[CH:36]=[N:37][CH:38]=[CH:39][CH:40]=2)[CH:34]=1)=[O:9]

Participants

6

Reactant 4

HCID 62365Isobutyl chloroformateHCID 75717Butanoic acid, 4-(dimethylamino)-4-oxo-HCID 81531DiisopropylethylamineHCID 67499640HCID 67499640, compound

Product 1

HCID 118023801HCID 118023801, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To an ice cold solution of 4-(dimethylamino)-4-oxobutanoic acid (0.174 g, 1.20 mmol) in CH2Cl2 (2 mL) was added DIPEA (0.208 mL, 1.120 mmol) followed by isobutyl chloroformate (0.138 mL, 1.06 mmol). The mixture was stirred for 10 minutes, and the resulting mixed anhydride was added to a solution of N,3-dimethyl-1-(pyridin-3-yl)-1H-pyrazol-4-amine (0.100 g, 0.531 mmol) in CH2Cl2 (0.66 mL). The reaction mixture was stirred at room temperature (about 22° C.) for one hour. The crude reaction mixture was concentrated and purified via reverse phase column chromatography (0%-100% acetonitrile (MeCN)/water) to give the desired product F62 as a white solid (0.155 g, 83%).

Workup

  1. stirringThe reaction mixture was stirred at room temperature (about 22° C.) for one hour
  2. customThe crude reaction mixture
  3. concentrationwas concentrated
  4. custompurified via reverse phase column chromatography (0%-100% acetonitrile (MeCN)/water)

Sources & evidence

ORD record
ord-54184d858a9441dbb8b7bde39f656dd9
Source dataset
uspto-grants-2016_03
Patent number
US09295260B2

Reaction notes

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