Trifluoroacetic acid → HCID 178420911, compound

HRID 1919175Notes

Reaction equation

HRID 1919175 reaction equation
C(O)(C(F)(F)F)=O.C(OC([N:15]1[CH2:19][CH2:18][CH2:17][C@H:16]1[C:20]1[NH:21][C:22]([C:25]2[S:29][C:28]([C:30]3[S:31][C:32]([C:35]4[N:36]=[C:37]([C@@H:40]5[CH2:44][CH2:43][CH2:42][N:41]5C(OC(C)(C)C)=O)[NH:38][CH:39]=4)=[CH:33][N:34]=3)=[N:27][CH:26]=2)=[CH:23][N:24]=1)=O)(C)(C)C>ClCCl>[NH:41]1[CH2:42][CH2:43][CH2:44][C@H:40]1[C:37]1[NH:38][CH:39]=[C:35]([C:32]2[S:31][C:30]([C:28]3[S:29][C:25]([C:22]4[N:21]=[C:20]([C@@H:16]5[CH2:17][CH2:18][CH2:19][NH:15]5)[NH:24][CH:23]=4)=[CH:26][N:27]=3)=[N:34][CH:33]=2)[N:36]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 178451928HCID 178451928, compound

Product 1

HCID 178420911HCID 178420911, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

TFA (1.0 mL, 13 mmol) was added to a stirred solution of tert-butyl (2S)-2-(4-(5′-(2-((2S)-1-(tert-butoxycarbonyl)-2-pyrrolidinyl)-1H-imidazol-5-yl)-2,2′-bi-1,3-thiazol-5-yl)-1H-imidazol-2-yl)-1-pyrrolidinecarboxylate (55 mg, 0.086 mmol) in dichloromethane (5 mL) and the reaction mixture was stirred at room temperature for 2 h. The volatiles were removed under vacuum and the crude product was purified by preparative HPLC (Waters Sunfire C18 column 30×150 mm 5 u, eluted with a gradient of 10 to 100% acetonitrile/water/0.1% TFA). Fractions containing the desired product were filtered through a Strata XC MCX cartridge. The cartridge was washed with methanol and the compound was released from the cartridge by washing the column with a 2M ammonia in methanol solution. The filtrate was evaporated under reduced pressure to yield 5,5′-bis(2-((2S)-2-pyrrolidinyl)-1H-imidazol-4-yl)-2,2′-bi-1,3-thiazole (39 mg, 0.085 mmol, 99% yield) as an orange solid.

Workup

  1. customThe volatiles were removed under vacuum
  2. customthe crude product was purified by preparative HPLC (Waters Sunfire C18 column 30×150 mm 5 u
  3. washeluted with a gradient of 10 to 100% acetonitrile/water/0.1% TFA)
  4. additionFractions containing the desired product
  5. filtrationwere filtered through a Strata XC MCX cartridge
  6. washThe cartridge was washed with methanol
  7. washby washing the column with a 2M ammonia in methanol solution
  8. customThe filtrate was evaporated under reduced pressure

Sources & evidence

ORD record
ord-00ef622c56e445f4880656992bd40d5a
Source dataset
uspto-grants-2013_12
Patent number
US08618153B2

Reaction notes

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