Diisopropylethylamine → HCID 89486743, compound

HRID 878413Notes

Reaction equation

HRID 878413 reaction equation
Cl[C:2]1[N:7]=[CH:6][C:5]([C:8]#[N:9])=[C:4]([NH:10][C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([CH3:17])[N:12]=2)[CH:3]=1.[CH2:18]([NH2:23])[CH:19]([NH2:22])[CH2:20][CH3:21].C(N(CC)C(C)C)(C)C>CN1C(=O)CCC1>[NH2:22][CH:19]([CH2:20][CH3:21])[CH2:18][NH:23][C:2]1[N:7]=[CH:6][C:5]([C:8]#[N:9])=[C:4]([NH:10][C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([CH3:17])[N:12]=2)[CH:3]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 138231Butane-1,2-diamineHCID 89486728HCID 89486728, compound

Product 1

HCID 89486743HCID 89486743, compound

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 6-chloro-4-[(6-methylpyridin-2-yl)amino]pyridine-3-carbonitrile (PrepEx 1.3) (38 mg, 0.16 mmol) in NMP (1 mL) was added butane-1,2-diamine (107 mg, 1.21 mmol) and N,N-diisopropylethylamine (0.163 mL, 0.932 mmol). The reaction mixture was heated to 100° C. After 16 hours, the reaction mixture was allowed to cool to room temperature, filtered, and purified directly via reverse phase HPLC (acetonitrile/water with 0.1% TFA, linear gradient) to afford 6-[(2-aminobutyl)amino]-4-[(6-methylpyridin-2-yl)amino]pyridine-3-carbonitrile. MS ESI calc'd. for C16H21N6 [M+H]+ 297. found 297.

Workup

  1. temperatureto cool to room temperature
  2. filtrationfiltered
  3. custompurified directly via reverse phase HPLC (acetonitrile/water with 0.1% TFA, linear gradient)

Sources & evidence

ORD record
ord-f480e558d86840059d1d011c21071897
Source dataset
uspto-grants-2015_03
Patent number
US08987456B2

Reaction notes

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