Trifluoroacetic acid → HCID 46240475, compound

HRID 410347Notes

Reaction equation

HRID 410347 reaction equation
C(OC(=O)[N:7]=[C:8]1[N:12]([CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[N:20]2[CH2:25][CH2:24][N:23]([CH2:26][C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=3[C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)[CH2:22][CH2:21]2)[C:11]2[CH:39]=[CH:40][CH:41]=[CH:42][C:10]=2[N:9]1[CH2:43][CH2:44][CH2:45][O:46][C:47]1[CH:52]=[CH:51][C:50]([F:53])=[CH:49][CH:48]=1)(C)(C)C.C(O)(C(F)(F)F)=O>ClCCl>[C:28]1([C:33]2[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=2)[CH:29]=[CH:30][CH:31]=[CH:32][C:27]=1[CH2:26][N:23]1[CH2:22][CH2:21][N:20]([C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=2[CH2:13][N:12]2[C:11]3[CH:39]=[CH:40][CH:41]=[CH:42][C:10]=3[N:9]([CH2:43][CH2:44][CH2:45][O:46][C:47]3[CH:48]=[CH:49][C:50]([F:53])=[CH:51][CH:52]=3)[C:8]2=[NH:7])[CH2:25][CH2:24]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67428842[1-(2-(4-Biphenyl-2-ylmethyl-piperazin-1-yl)-benzyl]-3-[3-(4-fluoro-phenoxy)-propyl]-1,3-dihydro-benzoimidazol-ylidene]-carbamic acid tert-butyl ester

Product 1

HCID 46240475HCID 46240475, compoundYield 3.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To [1-[2-(4-biphenyl-2-ylmethyl-piperazin-1-yl)-benzyl]-3-[3-(4-fluoro-phenoxy)-propyl]-1,3-dihydro-benzoimidazol-ylidene]-carbamic acid tert-butyl ester (100 mg, 0.14 mmol) at rt was added 25% TFA in dichloromethane (5 ml). The reaction was stirred for 1 h and then concentrated under reduced pressure. The crude product was purified by preparative HPLC and then partitioned between saturated NaHCO3 and dichloromethane. The organic phase was separated, washed with H2O, dried (Na2SO4), filtered and concentrated under reduced pressure to provide 1-[2-(4-biphenyl-2-ylmethyl-piperazin-1-yl)-benzyl]-3-[3-(4-fluoro-phenoxy)-propyl]-1,3-dihydro-benzoimidazol-2-ylideneamine (2.8 mg, 3%). HPLC-MS 626 [M+1]+, 324.

Workup

  1. concentrationconcentrated under reduced pressure
  2. customThe crude product was purified by preparative HPLC
  3. custompartitioned between saturated NaHCO3 and dichloromethane
  4. customThe organic phase was separated
  5. washwashed with H2O
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-0fcd280f5a0248db8265ec142c52e0b4
Source dataset
uspto-grants-2014_06
Patent number
US08759520B2

Reaction notes

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