Trifluoroacetic acid → HCID 178517351, compound

HRID 1805332Notes

Reaction equation

HRID 1805332 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C@H:8]2[C@@:10]3([C:18]4[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=4)[N:12]([C:19]4[N:20]=[CH:21][N:22](C(C5C=CC=CC=5)(C5C=CC=CC=5)C5C=CC=CC=5)[CH:23]=4)[C:11]3=[O:43])[CH2:9]2)=[CH:4][CH:3]=1.C(O)(C(F)(F)F)=O.C([O-])(O)=O.[Na+]>C(Cl)Cl.O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C@H:8]2[C@@:10]3([C:18]4[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=4)[N:12]([C:19]4[N:20]=[CH:21][NH:22][CH:23]=4)[C:11]3=[O:43])[CH2:9]2)=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 58305304(1R,2S)-2-(4-chlorophenyl)-1'-(1-trityl-1 H-imidazol-4-yl)spiro[cyclopropane-1,3'-indolin]-2'-one

Product 1

HCID 178517351HCID 178517351, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of racemic (1S,2R) and (1R,2S)-2-(4-chlorophenyl)-1′-(1-trityl-1H-imidazol-4-yl)spiro[cyclopropane-1,3′-indolin]-2′-one (115 mg, 0.2 mmol) in DCM (2 mL) and water (0.5 mL) was added TFA (0.1 mL) dropwise at 0° C. The mixture was stirred for 14 hours at room temperature. The mixture was poured into the sat. aqueous NaHCO3 solution, extracted with DCM (3×10 mL), dried and concentrated to give the title product. The residue was dissolved in 2 mL of DMF. Purification by preparative HPLC gave the title compound as white powder (60 mg, 89%). LC/MS m/e calcd. for C19H14ClN3O: 335, observed (M+H)+: 336.1 1H NMR (400 MHz, DMSO-d6) δppm 2.13 (dd, J=9.09, 5.05 Hz, 1 H) 2.42 (dd, J=8.08, 4.80 Hz, 1 H) 3.23 (t, J=8.72 Hz, 1 H) 6.20 (d, J=7.58 Hz, 1 H) 6.81 (t, J=7.20 Hz, 1 H) 7.16 (t, J=7.83 Hz, 1 H) 7.30-7.45 (m, 5 H) 7.66 (s, 1 H) 8.27 (s, 1 H). MS calcd. for C19H14ClN3O 335, obsd. (ESI+) [(M+H)+] 336.3.

Workup

  1. extractionextracted with DCM (3×10 mL)
  2. customdried
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-5d918868f37947f789f0b777cad3cc6d
Source dataset
uspto-grants-2013_01
Patent number
US08354443B2

Reaction notes

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