Trifluoroacetic acid → HCID 86688454, compound

HRID 2359142Notes

Reaction equation

HRID 2359142 reaction equation
FC(F)(F)C(O)=O.[Cl:8][C:9]1[CH:14]=[C:13]([Cl:15])[CH:12]=[CH:11][C:10]=1[C@H:16]([N:18]1[C:22]2[CH:23]=[C:24]([N:27]3[CH2:32][CH2:31][N:30]([C:33]([C@H:35]4[CH2:39][CH2:38][CH2:37][N:36]4C(OC(C)(C)C)=O)=[O:34])[C@H:29]([CH3:47])[CH2:28]3)[CH:25]=[CH:26][C:21]=2[N:20]=[N:19]1)[CH3:17]>ClCCl>[Cl:8][C:9]1[CH:14]=[C:13]([Cl:15])[CH:12]=[CH:11][C:10]=1[C@H:16]([N:18]1[C:22]2[CH:23]=[C:24]([N:27]3[CH2:32][CH2:31][N:30]([C:33]([C@H:35]4[CH2:39][CH2:38][CH2:37][NH:36]4)=[O:34])[C@H:29]([CH3:47])[CH2:28]3)[CH:25]=[CH:26][C:21]=2[N:20]=[N:19]1)[CH3:17]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86688456HCID 86688456, compound

Product 1

HCID 86688454HCID 86688454, compoundYield 30%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic acid (0.5 mL) was added to a solution of (R)-tert-butyl 2-((R)-4-(1-((R)-1-(2,4-dichlorophenyl)ethyl)-1H-benzo[d][1,2,3]triazol-6-yl)-2-methylpiperazine-1-carbonyl)pyrrolidine-1-carboxylate (0.075 g, 0.13 mol) in dichloromethane (1.5 mL) and the mixture was stirred at room temperature for 1 h. Excess solvent was removed in vacuo, and the residue was diluted with dichloromethane (15 mL). The organic layer was neutralized with saturated aqueous sodium bicarbonate, and the aqueous layer was further extracted with dichloromethane (2×15 mL). The combined organic layers were dried (Na2SO4), filtered, and concentrated in vacuo. The crude product was purified by flash chromatography (SiO2, 0-30% methanol in dichloromethane) to give the title compound as a white solid (0.022, 0.037 mol, 30%). 1H NMR (400 MHz, CDCl3) δ 7.87 (d, J=8.8 Hz, 1 H), 7.41 (dd, J=0.8, 0.8 Hz, 1 H), 7.15-7.14 (m, 2 H), 7.02 (dd, J=2.4, 9.2 Hz, 1 H), 6.53 (s, 1 H), 6.23 (q, J=7.2 Hz, 1 H), 4.90-4.84 (m, 1 H), 4.58-4.54 (m, 1 H), 4.32-4.28 (m, 1 H), 3.97-3.74 (m, 3 H), 3.56-3.44 (m, 3 H), 3.20-3.16 (m, 1 H), 2.97-2.94 (m, 1 H), 2.85-2.80 (m, 1 H), 2.14 (d, J=6.8 Hz, 3 H), 1.82-1.71 (m, 3 H), 1.47-1.25 (m, 2 H); MS: (ES) m/z calculated for C24H29Cl2N6O [M+H]+ 487.2 found 487.3.

Workup

  1. customExcess solvent was removed in vacuo
  2. additionthe residue was diluted with dichloromethane (15 mL)
  3. extractionthe aqueous layer was further extracted with dichloromethane (2×15 mL)
  4. dry with materialThe combined organic layers were dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe crude product was purified by flash chromatography (SiO2, 0-30% methanol in dichloromethane)

Sources & evidence

ORD record
ord-99db8124a2b64867bd72f667c2dde105
Source dataset
uspto-grants-2014_04
Patent number
US08685959B2

Reaction notes

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