Trifluoroacetic acid → HCID 53233526, compound

HRID 1919169Notes

Reaction equation

HRID 1919169 reaction equation
C(O)(C(F)(F)F)=O.[S:8]1[C:12]([C:13]2[S:17][C:16]([C:18]3[NH:22][C:21]([C@@H:23]4[CH2:27][CH2:26][CH2:25][N:24]4C(OC(C)(C)C)=O)=[N:20][CH:19]=3)=[N:15][CH:14]=2)=[CH:11][N:10]=[C:9]1[C:35]1[NH:39][C:38]([C@@H:40]2[CH2:44][CH2:43][CH2:42][N:41]2C(OC(C)(C)C)=O)=[N:37][CH:36]=1>ClCCl>[NH:41]1[CH2:42][CH2:43][CH2:44][C@H:40]1[C:38]1[NH:39][C:35]([C:9]2[S:8][C:12]([C:13]3[S:17][C:16]([C:18]4[NH:22][C:21]([C@@H:23]5[CH2:27][CH2:26][CH2:25][NH:24]5)=[N:20][CH:19]=4)=[N:15][CH:14]=3)=[CH:11][N:10]=2)=[CH:36][N:37]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acid2×HCID 53233525HCID 53233525, compound

Product 1

HCID 53233526HCID 53233526, compoundYield 58.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

TFA (2 mL, 26.0 mmol) was added to a stirred solution of di-tert-butyl (2S,2′S)-2,2′-(5,5′-bi-1,3-thiazole-2,2′-diylbis(1H-imidazole-5,2-diyl))di(1-pyrrolidinecarboxylate) (450 mg, 0.704 mmol) in dichloromethane (15 mL) at room temperature. The reaction mixture was stirred for 2 h, additional TFA (2 mL, 26.0 mmol) was added and the mixture was stirred for an additional 2 h. The reaction was concentrated in vacuo and the residue was dissolved in methanol and filtered through a Strata XC MCX cartridge. The cartridge was washed with methanol and then the compound was released from the cartridge by washing with a solution of 2M ammonia in methanol. The filtrate was evaporated under reduced pressure to give 2,2′-bis(2-((2S)-2-pyrrolidinyl)-1H-imidazol-5-yl)-5,5′-bi-1,3-thiazole (181 mg) as an orange solid.

Workup

  1. stirringthe mixture was stirred for an additional 2 h
  2. concentrationThe reaction was concentrated in vacuo
  3. dissolutionthe residue was dissolved in methanol
  4. filtrationfiltered through a Strata XC MCX cartridge
  5. washThe cartridge was washed with methanol
  6. washby washing with a solution of 2M ammonia in methanol
  7. customThe filtrate was evaporated under reduced pressure

Sources & evidence

ORD record
ord-b37e40cd5473495eb72fd17f87678a0c
Source dataset
uspto-grants-2013_12
Patent number
US08618153B2

Reaction notes

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