Isopropylamine → HCID 44544618, compound

HRID 523874Notes

Reaction equation

HRID 523874 reaction equation
Cl[C:2]1[N:7]=[C:6]([C:8]([OH:10])=[O:9])[CH:5]=[CH:4][C:3]=1[C:11]#[N:12].[CH:13](N)(C)C.[F-].[K+].C[N:20]1[CH2:24][CH2:23][CH2:22]C1=O>O>[C:11]([C:3]1[CH:4]=[CH:5][C:6]([C:8]([OH:10])=[O:9])=[N:7][C:2]=1[NH:20][CH2:24][CH:23]([CH3:13])[CH3:22])#[N:12]

Participants

6

Reactant 4

HCID 6363IsopropylamineHCID 13387N-methyl-2-pyrrolidoneHCID 522689Potassium FluorideHCID 534332396-Chloro-5-cyanopyridine-2-carboxylic acid

Product 1

HCID 44544618HCID 44544618, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
95 °C

Procedure

A mixture of 6-chloro-5-cyanopicolinic acid (30 mg, 0.16 mmol), isopropylamine (20 ul, 0.23 mmol), and KF (28 mg, 0.48 mmol) in N-methylpyrrolidinone (1 ml) was heated for 18 hrs at 95° C. The mixture was diluted with water (4 ml) and standed overnight. The resulting precipitate was collected by filtration and dried under vacuum to afford 25 mg (75%) of the desired product 70. 1H NMR (600 MHz, DMSO-d6) δ 13.2 (s, 1H), 8.03 (d, 1H, J=7.8 Hz), 7.25-7.21 (m, 1H), 7.17 (d, 1H, J=7.8 Hz), 3.26-3.24 (m, 2H), 1.99-1.95 (m, 1H), 0.89 (d, 6H, 6.6 Hz). MS: m/z Calcd 219.2 Found MH+ 220.1

Workup

  1. filtrationThe resulting precipitate was collected by filtration
  2. customdried under vacuum

Sources & evidence

ORD record
ord-a36c47e17e4c420eabe56afd835b53d7
Source dataset
uspto-grants-2016_05
Patent number
US09340505B2

Reaction notes

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