Trifluoroacetic acid → 3-{3-[3-(3-{4-[2-(4-Chloro-phenyl)-5,5-dimethyl-cyclohex-1-enylmethyl]-piperazin-1-yl}-benzyl)-2-imino-2,3-dihydro-benzoimidazol-1-yl]-propoxy}-benzoic acid

HRID 410371Notes

Reaction equation

HRID 410371 reaction equation
C(OC([N:8]=[C:9]1[N:13]([CH2:14][CH2:15][CH2:16][O:17][C:18]2[CH:19]=[C:20]([CH:24]=[CH:25][CH:26]=2)[C:21]([OH:23])=[O:22])[C:12]2[CH:27]=[CH:28][CH:29]=[CH:30][C:11]=2[N:10]1[CH2:31][C:32]1[CH:37]=[CH:36][CH:35]=[C:34]([N:38]2[CH2:43][CH2:42][N:41]([CH2:44][C:45]3[CH2:50][C:49]([CH3:52])([CH3:51])[CH2:48][CH2:47][C:46]=3[C:53]3[CH:58]=[CH:57][C:56]([Cl:59])=[CH:55][CH:54]=3)[CH2:40][CH2:39]2)[CH:33]=1)=O)(C)(C)C.C(O)(C(F)(F)F)=O>ClCCl>[Cl:59][C:56]1[CH:55]=[CH:54][C:53]([C:46]2[CH2:47][CH2:48][C:49]([CH3:52])([CH3:51])[CH2:50][C:45]=2[CH2:44][N:41]2[CH2:40][CH2:39][N:38]([C:34]3[CH:33]=[C:32]([CH:37]=[CH:36][CH:35]=3)[CH2:31][N:10]3[C:11]4[CH:30]=[CH:29][CH:28]=[CH:27][C:12]=4[N:13]([CH2:14][CH2:15][CH2:16][O:17][C:18]4[CH:19]=[C:20]([CH:24]=[CH:25][CH:26]=4)[C:21]([OH:23])=[O:22])[C:9]3=[NH:8])[CH2:43][CH2:42]2)=[CH:58][CH:57]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 674299233-{3-[2-[Tert-butoxycarbonylimino]-3-(3-{4-[2-(4-chloro-phenyl)-5,5-dimethyl-cyclohex-1-enylmethyl]-piperazin-1-yl}-benzyl)-2,3-dihydro-benzoimidazol-1-yl]-propoxy)-benzoic acid

Product 1

HCID 585649923-{3-[3-(3-{4-[2-(4-Chloro-phenyl)-5,5-dimethyl-cyclohex-1-enylmethyl]-piperazin-1-yl}-benzyl)-2-imino-2,3-dihydro-benzoimidazol-1-yl]-propoxy}-benzoic acidYield 6.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-{3-[2-[tert-butoxycarbonylimino]-3-(3-{4-[2-(4-chloro-phenyl)-5,5-dimethyl-cyclohex-1-enylmethyl]-piperazin-1-yl}-benzyl)-2,3-dihydro-benzoimidazol-1-yl]-propoxy}-benzoic acid (0.15 g, 0.18 mmol) in dichloromethane (2.25 ml) at rt was added TFA (0.75 ml). The reaction was stirred at rt for 1 h and then concentrated under reduced pressure. The crude product was purified by preparative HPLC to provide 3-{3-[3-(3-{4-[2-(4-chloro-phenyl)-5,5-dimethyl-cyclohex-1-enylmethyl]-piperazin-1-yl}-benzyl)-2-imino-2,3-dihydro-benzoimidazol-1-yl]-propoxy}-benzoic acid (8.5 mg, 6%). HPLC-MS 718 [M+1]+, 360.

Workup

  1. concentrationconcentrated under reduced pressure
  2. customThe crude product was purified by preparative HPLC

Sources & evidence

ORD record
ord-1f4364fd3d5d4762bb844ce96673981c
Source dataset
uspto-grants-2014_06
Patent number
US08759520B2

Reaction notes

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