Isopropylamine → HCID 86629520, compound

HRID 1711152Notes

Reaction equation

HRID 1711152 reaction equation
[Cl:1][C:2]1[N:10]=[C:9]([C:11]#[N:12])[CH:8]=[C:7]([CH3:13])[C:3]=1[C:4]([OH:6])=[O:5].CCN=C=N[CH2:19][CH2:20][CH2:21]N(C)C.C1C=CC2N([OH:34])N=NC=2C=1.CCN(C(C)C)C(C)C.C(N)(C)C>Cl.CN(C=O)C>[Cl:1][C:2]1[N:10]=[C:9]([C:11](=[O:34])[NH:12][CH:20]([CH3:21])[CH3:19])[CH:8]=[C:7]([CH3:13])[C:3]=1[C:4]([OH:6])=[O:5]

Participants

8

Reactant 5

HCID 6363IsopropylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 83680757HCID 83680757, compound

Product 1

HCID 86629520HCID 86629520, compoundYield 47.2%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
25 °C

Procedure

2-Chloro-6-cyano-4-methyl-nicotinic acid (0.315 g, 1.61 mmol) in concentrated HCl (8 ml) was heated at 100° C. for 45 minutes and then all solvent was removed in vacuo to yield a pale yellow crystalline solid. The crude solid, EDCI (0.339 g, 1.77 mmol) and HOBt (0.239 g, 1.77 mmol) were combined in DMF (8 ml) to give a pale yellow solution. To this solution was added DIPEA (1.85 ml, 10.6 mmol) followed by isopropylamine (137 μL, 1.61 mmol) and the resulting mixture was stirred at 25° C. for 16 hours. The reaction mixture was quenched with water (3 ml) and then dry loaded onto silica gel and purified using column chromatography (MeCN/MeOH/NH4OH, 8:1:1, v/v/v) to give 2-chloro-6-isopropylcarbamoyl-4-methyl-nicotinic acid (0.195 g, 47%).

Workup

  1. customall solvent was removed in vacuo
  2. customto yield a pale yellow crystalline solid
  3. customto give a pale yellow solution
  4. customThe reaction mixture was quenched with water (3 ml)
  5. customdry
  6. custompurified

Sources & evidence

ORD record
ord-897002243d2449af8fbc4c3f0fbf91c2
Source dataset
uspto-grants-2010_09
Patent number
US07790747B2

Reaction notes

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