Water → HCID 11960056, compound

HRID 1508398Notes

Reaction equation

HRID 1508398 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-8e223623994444358e38ecf1c1285d39
Source dataset
uspto-grants-2015_12
Patent number
US09221841B2

Reaction notes

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