Hydrochloric Acid → 2-amino-1-(2-(3-aminopropyl)-5-(2,5difluorophenyl)-2-phenyl-1,3,4-thiadiazol-3(2H)-yl)propan-1-one

HRID 512890Notes

Reaction equation

HRID 512890 reaction equation
[NH2:1][CH:2]([CH3:30])[C:3]([N:5]1[N:9]=[C:8]([C:10]2[CH:15]=[C:14]([F:16])[CH:13]=[CH:12][C:11]=2[F:17])[S:7][C:6]1([CH2:24][CH2:25][CH2:26][N:27]=[N+]=[N-])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=[O:4].Cl.N#N>CO.[Pd]>[NH2:1][CH:2]([CH3:30])[C:3]([N:5]1[N:9]=[C:8]([C:10]2[CH:15]=[C:14]([F:16])[CH:13]=[CH:12][C:11]=2[F:17])[S:7][C:6]1([CH2:24][CH2:25][CH2:26][NH2:27])[C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1)=[O:4]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 947NitrogenHCID 866048322-amino-1-(2-(3-azidopropyl)-5-(2,5-difluorophenyl)-2-phenyl-1,3,4-thiadiazol-3(2H)-yl)propan-1-one

Product 1

HCID 601398152-amino-1-(2-(3-aminopropyl)-5-(2,5difluorophenyl)-2-phenyl-1,3,4-thiadiazol-3(2H)-yl)propan-1-oneYield 87.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

2-Amino-1-(2-(3-azidopropyl)-5-(2,5-difluorophenyl)-2-phenyl-1,3,4-thiadiazol-3 (2H)-yl)propan-1-one (50 mg, 0.116 mmol) was dissolved in 5.0 mL of MeOH. HCl (0.46 ml, 0.464 mmol) was added followed by evacuation/re-vacuation with N2. Pd/C (12 mg, 0.011 mmol) was then added followed by H2 balloon. Following 40 hours at 23° C., the reaction was concentrated in vacuo, affording the product (41 mg, 87%) as a cream/yellow colored foam. MS ESI (+) m/z 405 (M+1) detected; 1H NMR (400 MHz, CD3OD) δ7.68 (m, 1H), 7.53 (m, 2H), 7.42 (t, 2H, J=9 Hz), 7.34 (m, 3H), 4.92 (m, 1H), 3.22 (m, 2H), 3.17 (m, 4H), 2.65 (m, 2H), 2.20 (m, 1H), 1.99 (m, 1H), 1.72 (d, 1.5H, J=8 Hz), 1.66 d, 1.5H, J=8 Hz).

Workup

  1. concentrationthe reaction was concentrated in vacuo

Sources & evidence

ORD record
ord-72336c0347b7458288cc53314d99f14e
Source dataset
uspto-grants-2015_08
Patent number
US09102639B2

Reaction notes

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