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

HRID 883103Notes

Reaction equation

HRID 883103 reaction equation
[N:1]([CH2:4][CH2:5][CH2:6][C:7]1([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[N:11]([C:12](=[O:23])[CH:13]([NH:15]C(=O)OC(C)(C)C)[CH3:14])[N:10]=[C:9]([C:24]2[CH:29]=[C:28]([F:30])[CH:27]=[CH:26][C:25]=2[F:31])[S:8]1)=[N+:2]=[N-:3].Cl>CCO>[NH2:15][CH:13]([CH3:14])[C:12]([N:11]1[N:10]=[C:9]([C:24]2[CH:29]=[C:28]([F:30])[CH:27]=[CH:26][C:25]=2[F:31])[S:8][C:7]1([CH2:6][CH2:5][CH2:4][N:1]=[N+:2]=[N-:3])[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)=[O:23]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 86604830tert-butyl 1-(2-(3-azidopropyl)-5-(2,5-difluorophenyl)-2-phenyl-1,3,4-thiadiazol-3(2H)-yl)-1-oxopropan-2-ylcarbamate

Product 1

HCID 866048322-amino-1-(2-(3-azidopropyl)-5-(2,5-difluorophenyl)-2-phenyl-1,3,4-thiadiazol-3(2H)-yl)propan-1-oneYield 95.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
23 °C

Procedure

tert-Butyl 1-(2-(3-azidopropyl)-5-(2,5-difluorophenyl)-2-phenyl-1,3,4-thiadiazol-3(2H)-yl)-1-oxopropan-2-ylcarbamate (70 mg, 0.131 mmol) was dissolved in 7.0 mL of EtOH. HCl (0.65 mL, 0.659 mmol) was then added and the reaction stirred at 23° C. for 4 hours. The reaction was then concentrated and purified by chromatography (2-10% MeOH/DCM), yielding the product (54 mg, 95%) as a yellow oil. MS ESI (+) m/z 431 (M+1) detected; 1H NMR (400 MHz, CD3OD) δ7.69 (m, 1H), 7.53 (d, 2H, J=8 Hz), 7.42 (t, 2H, J=7 Hz), 7.34 (m, 3H), 4.91 (m, 3H), 3.21 (m, 1H), 3.17 (m, 2H), 2.68 (m, 1H), 2.19 (m, 1H), 1.99 (m, 1H), 1.73 (d, 1.5H, J=8 Hz), 1.64 (d, 1.5H, J=8 Hz).

Workup

  1. concentrationThe reaction was then concentrated
  2. custompurified by chromatography (2-10% MeOH/DCM)

Sources & evidence

ORD record
ord-d09f3f9bf75a4ee1a3b88e07c2c4fa92
Source dataset
uspto-grants-2012_08
Patent number
US08236825B2

Reaction notes

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