Water → 2-Amino-4-((3-phenylpropyl)amino)nicotinonitrile

HRID 1615908Notes

Reaction equation

HRID 1615908 reaction equation
[N:1]([C:4]1[N:11]=[CH:10][CH:9]=[C:8]([NH:12][CH2:13][CH2:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:5]=1[C:6]#[N:7])=[N+]=[N-].O>O1CCCC1.CP(C)C>[NH2:1][C:4]1[N:11]=[CH:10][CH:9]=[C:8]([NH:12][CH2:13][CH2:14][CH2:15][C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)[C:5]=1[C:6]#[N:7]

Participants

5

Reactant 2

HCID 962WaterHCID 866965072-Azido-4-((3-phenylpropyl)amino)nicotinonitrile

Product 1

HCID 866965082-Amino-4-((3-phenylpropyl)amino)nicotinonitrileYield 34.6%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 68983TrimethylphosphineSolvent

Procedure

Prepared according to the methods above using 2-azido-4-((3-phenylpropyl)amino)nicotinonitrile (35 mg, 0.126 mmol) in tetrahydrofuran (1.5 mL), trimethylphosphine 1.0 M in tetrahydrofuran (0.629 mL, 0.629 mmol) and water (0.011 mL, 0.629 mmol) at rt for 3.5 hours to give the desired product as an off-white solid (11 mg). LC/MS (253, [M+H]); 1H NMR (400 MHz, CHLOROFORM-d) δ 7.85-7.78 (m, 1H), 7.37-7.29 (m, 2H), 7.26-7.23 (m, 1H), 7.22-7.16 (m, 2H), 5.92 (d, J=6.0 Hz, 1H), 5.17 (br. s., 2H), 4.94 (br. s., 1H), 3.30-3.20 (m, 2H), 2.74 (t, J=7.5 Hz, 2H), 2.00 (quin, J=7.3 Hz, 2H).

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-52f7b902dbe34918a00beef34e198fd3
Source dataset
uspto-grants-2014_07
Patent number
US08765767B2

Reaction notes

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