Water → (S)-2-Amino-4-((4-phenylbutan-2-yl)amino)nicotinonitrile

HRID 1615911Notes

Reaction equation

HRID 1615911 reaction equation
[N:1]([C:4]1[N:11]=[CH:10][CH:9]=[C:8]([NH:12][C@H:13]([CH2:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH3:14])[C:5]=1[C:6]#[N:7])=[N+]=[N-].O>C1COCC1.CP(C)C>[NH2:1][C:4]1[N:11]=[CH:10][CH:9]=[C:8]([NH:12][C@H:13]([CH2:15][CH2:16][C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH3:14])[C:5]=1[C:6]#[N:7]

Participants

5

Reactant 2

HCID 962WaterHCID 86696510(S)-2-Azido-4-((4-phenylbutan-2-yl)amino)nicotinonitrile

Product 1

HCID 86696511(S)-2-Amino-4-((4-phenylbutan-2-yl)amino)nicotinonitrileYield 68.4%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 68983TrimethylphosphineSolvent

Procedure

Prepared according to the methods above using (S)-2-azido-4-((4-phenylbutan-2-yl)amino)nicotinonitrile (59.1 mg, 0.192 mmol) in THF (2.0 mL), trimethylphosphine 1.0 M in tetrahydrofuran (0.960 mL, 0.960 mmol) and water (0.017 mL, 0.960 mmol) at rt for 3.5 hours to give the desired product as a white solid (35 mg). LC/MS (267, [M+H]+); 1H NMR (400 MHz, CHLOROFORM-d) δ 7.78 (d, J=6.3 Hz, 1H), 7.35-7.26 (m, 2H), 7.26-7.19 (m, 1H), 7.19-7.11 (m, 2H), 5.83 (d, J=6.3 Hz, 1H), 5.13 (br. s., 2H), 4.70 (d, J=8.0 Hz, 1H), 3.65-3.51 (m, 1H), 2.71 (t, J=7.7 Hz, 2H), 1.98-1.80 (m, 2H), 1.32-1.23 (m, 3H).

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-8fc6250b84944dc9abe20029328480cd
Source dataset
uspto-grants-2014_07
Patent number
US08765767B2

Reaction notes

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