Water → HCID 11960056, compound

HRID 1713459Notes

Reaction equation

HRID 1713459 reaction equation
[N:1]([CH2:4][CH2:5][CH2:6][C:7]1([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[N:11]([C:12]2[S:13][C:14]([Br:17])=[N:15][N:16]=2)[N:10]=[C:9]([C:18]2[CH:23]=[C:22]([F:24])[CH:21]=[CH:20][C:19]=2[F:25])[S:8]1)=[N+]=[N-].O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1COCC1>[Br:17][C:14]1[S:13][C:12]([N:11]2[N:10]=[C:9]([C:18]3[CH:23]=[C:22]([F:24])[CH:21]=[CH:20][C:19]=3[F:25])[S:8][C:7]2([CH2:6][CH2:5][CH2:4][NH2:1])[C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)=[N:16][N:15]=1

Participants

5

Reactant 3

HCID 962WaterHCID 11776TriphenylphosphineHCID 86608778HCID 86608778, compound

Product 1

HCID 11960056HCID 11960056, compoundYield 53%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
23 °C

Procedure

2-(2-(3-azidopropyl)-5-(2,5-difluorophenyl)-2-phenyl-1,3,4-thiadiazol-3(2H)-yl)-5-bromo-1,3,4-thiadiazole (0.006 g, 0.011 mol) was dissolved in 0.25 mL THF, followed by addition of water (0.015 g, 15 μL) and triphenylphosphine (0.015 g, 0.057 mmol), and the reaction mixture was stirred at 23° C. overnight. The crude mixture was purified by directly loading onto a preparative TLC plate and eluting first with 12:1 (DCM:MeOH), followed by a second elution with 10:1 (DCM:MeOH) (both with NH4OH present), to afford the desired product (0.003 g, 53%). MS ESI (+) m/z 495/497 (M+1) detected; 1H NMR (400 MHz, CDCl3) δ 7.52 (m, 3H), 7.35 (t, 2H, J=7.6 Hz), 7.30 (d, 1H, J=7.2 Hz), 7.12 (m, 2H), 3.46 (m, 1H), 2.65 (m, 6H), 2.05 (m, 1H), 1.61 (m, 1H).

Workup

  1. customThe crude mixture was purified
  2. washeluting first with 12:1 (DCM:MeOH)
  3. washfollowed by a second elution with 10:1 (DCM:MeOH) (both with NH4OH present),

Sources & evidence

ORD record
ord-58e242d7d7a24d7fbcb2ffd45f2c83f4
Source dataset
uspto-grants-2010_09
Patent number
US07795282B2

Reaction notes

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