Trifluoroacetic acid → HCID 86642501, compound

HRID 1631999Notes

Reaction equation

HRID 1631999 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([NH:14][CH:15]2[CH2:20][CH2:19][N:18]([C:21](=[O:52])[CH:22]([N:29]3[C:33]4[CH:34]=[C:35]([C:38]#[N:39])[CH:36]=[CH:37][C:32]=4[N:31]([S:40]([C:43]4[CH:48]=[CH:47][C:46]([O:49][CH3:50])=[CH:45][CH:44]=4)(=[O:42])=[O:41])[C:30]3=[O:51])[C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[CH2:17][CH2:16]2)[CH2:10][CH2:9]1)=O)(C)(C)C.[F:53][C:54]([F:59])([F:58])[C:55]([OH:57])=[O:56]>C(Cl)Cl>[F:53][C:54]([F:59])([F:58])[C:55]([OH:57])=[O:56].[CH3:50][O:49][C:46]1[CH:45]=[CH:44][C:43]([S:40]([N:31]2[C:32]3[CH:37]=[CH:36][C:35]([C:38]#[N:39])=[CH:34][C:33]=3[N:29]([CH:22]([C:23]3[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=3)[C:21](=[O:52])[N:18]3[CH2:17][CH2:16][CH:15]([NH:14][CH:11]4[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]4)[CH2:20][CH2:19]3)[C:30]2=[O:51])(=[O:41])=[O:42])=[CH:48][CH:47]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 66754789HCID 66754789, compound

Product 1

HCID 86642501HCID 86642501, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-(1-{2-[6-cyano-3-(4-methoxy-benzenesulfonyl)-2-oxo-2,3-dihydrobenzoimidazol-1-yl]-2-phenyl-acetyl}-piperidin-4-ylamino]-piperidine-1-carboxylic acid tert-butyl ester (100 mg, 0.14 mmol) in CH2Cl2 (2 mL) was added trifluoroacetic acid (2 mL). The reaction mixture was stirred at room temperature for 2 hours, concentrated in vacuo and co-evaporated the solvent with toluene (3×). The residue was purified by preparative RP-HPLC (eluent: gradient from 10% to 80% acetonitrile in water, 0.1% trifluoroacetic acid as modulator) to afford 1-(4-methoxybenzenesulfonyl)-2-oxo-3-{2-oxo-1-phenyl-2-[4-(piperidin-4-ylamino)-piperidin-1-yl]ethyl}-2,3-dihydro-1H-benzoimidazole-5-carbonitrile; compound with trifluoroacetic acid (70 mg, 67%) as a white solid.

Workup

  1. concentrationconcentrated in vacuo
  2. customThe residue was purified by preparative RP-HPLC (eluent: gradient from 10% to 80% acetonitrile in water, 0.1% trifluoroacetic acid as modulator)

Sources & evidence

ORD record
ord-62ca46f439da44df8a9097b068f2fa42
Source dataset
uspto-grants-2014_07
Patent number
US08791148B2

Reaction notes

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