Diisopropylethylamine → (S)-2-Bromo-4-((4-phenylbutan-2-yl)amino)nicotinonitrile

HRID 1615909Notes

Reaction equation

HRID 1615909 reaction equation
[Br:1][C:2]1[N:9]=[CH:8][CH:7]=[C:6](Br)[C:3]=1[C:4]#[N:5].[CH3:11][C@H:12]([NH2:21])[CH2:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.CCN(C(C)C)C(C)C>CN(C=O)C>[Br:1][C:2]1[N:9]=[CH:8][CH:7]=[C:6]([NH:21][C@H:12]([CH2:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH3:11])[C:3]=1[C:4]#[N:5]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 69945644-Phenylbutan-2-amine, (S)-HCID 574595912,4-Dibromopyridine-3-carbonitrile

Product 1

HCID 86696509(S)-2-Bromo-4-((4-phenylbutan-2-yl)amino)nicotinonitrileYield 60.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Prepared according to the methods above using 2,4-dibromonicotinonitrile (100 mg, 0.382 mmol), (S)-1-Methyl-3-phenyl-propylamine (58.1 mg, 0.382 mmol) and Hunig's Base (0.080 mL, 0.458 mmol) in DMF (1.5 mL) at 120° C. for 30 min to give the desired product as a clear oil (76 mg). LC/MS (316/318, [M−H]/[M+H]+); 1H NMR (400 MHz, CHLOROFORM-d) δ 8.05 (d, J=5.5 Hz, 1H), 7.33-7.25 (m, 2H), 7.23-7.15 (m, 3H), 6.81 (d, J=5.3 Hz, 1H), 5.06 (br. s., 1H), 4.33 (dt, J=14.0, 6.9 Hz, 1H), 2.71 (t, J=8.0 Hz, 2H), 1.98-1.83 (m, 2H), 1.32-1.25 (m, 3H).

Workup

  1. customPrepared
  2. customat 120° C.
  3. customfor 30 min

Sources & evidence

ORD record
ord-76ab4146273f458ba26152e2db572a76
Source dataset
uspto-grants-2014_07
Patent number
US08765767B2

Reaction notes

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