Trifluoroacetic acid → HCID 59457844, compound

HRID 1711779Notes

Reaction equation

HRID 1711779 reaction equation
C(OC([N:8]1[CH2:12][CH2:11][CH2:10][CH:9]1[CH2:13][N:14]1[C:18]2[CH:19]=[C:20]([C:23]3[N:30]4[C:26]([S:27][CH:28]=[CH:29]4)=[N:25][C:24]=3[C:31]3[CH:36]=[CH:35][C:34]([F:37])=[CH:33][CH:32]=3)[CH:21]=[CH:22][C:17]=2[N:16]=[C:15]1[NH2:38])=O)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[F:37][C:34]1[CH:35]=[CH:36][C:31]([C:24]2[N:25]=[C:26]3[N:30]([C:23]=2[C:20]2[CH:21]=[CH:22][C:17]4[N:16]=[C:15]([NH2:38])[N:14]([CH2:13][CH:9]5[CH2:10][CH2:11][CH2:12][NH:8]5)[C:18]=4[CH:19]=2)[CH:29]=[CH:28][S:27]3)=[CH:32][CH:33]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 59457852HCID 59457852, compound

Product 1

HCID 59457844HCID 59457844, compoundYield 68.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-{2-amino-6-[6-(4-fluorophenyl)-imidazo[2,1-b]thiazol-5-yl]benzimidazol-1-ylmethyl}pyrrolidine-1-carboxylic acid tert-butyl ester (0.12 g, 0.22 mmol; Example #G.1.16) in DCM (2.7 mL) was added TFA (0.30 mL). After about 18 h, the reaction was concentrated under reduced pressure then saturated aqueous NaHCO3 was added and extracted with DCM/MeOH (9:1, 3×30 mL). The combined organic layers were washed with brine, dried over Na2SO4, decanted, and concentrated. The crude material was purified by silica gel chromatography using DCM/MeOH/NH4OH (stepwise gradient 980:18:2 to 950:45:5). After concentration of the column fractions, the residue was dissolved in DCM and heptane was added until a precipitate formed. The mixture was then concentrated under reduced pressure to give the title compound (0.065 g, 67%): LC/MS (Table 1, Method b) Rt, =1.47 min; MS m/z: 433.1 (M+H)+.

Workup

  1. concentrationthe reaction was concentrated under reduced pressure
  2. additionsaturated aqueous NaHCO3 was added
  3. extractionextracted with DCM/MeOH (9:1, 3×30 mL)
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over Na2SO4
  6. customdecanted
  7. concentrationconcentrated
  8. customThe crude material was purified by silica gel chromatography
  9. dissolutionAfter concentration of the column fractions, the residue was dissolved in DCM
  10. additionheptane was added until a precipitate
  11. customformed
  12. concentrationThe mixture was then concentrated under reduced pressure

Sources & evidence

ORD record
ord-f31354b27a1b449f929736d8833b0112
Source dataset
uspto-grants-2010_09
Patent number
US07790741B2

Reaction notes

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