Trifluoroacetic acid → Methyl 3-[(6-bromo-2,3-dihydro-2-oxo-1H-indol-4-yl)methyl]-2,3-dihydro-2-oxo-β-propyl-1H-benzimidazole-1-propanoate

HRID 1747460Notes

Reaction equation

HRID 1747460 reaction equation
C(OC([N:8]1[C:16]2[C:11](=[C:12]([CH2:18][N:19]3[C:23]4[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=4[N:21]([CH:28]([CH2:32][C:33]([O:35][CH3:36])=[O:34])[CH2:29][CH2:30][CH3:31])[C:20]3=[O:37])[CH:13]=[C:14]([Br:17])[CH:15]=2)[CH:10]=[C:9]1[O:38]C(OC(C)(C)C)=O)=O)(C)(C)C.FC(F)(F)C(O)=O>ClCCl>[CH3:36][O:35][C:33](=[O:34])[CH2:32][CH:28]([N:21]1[C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=2[N:19]([CH2:18][C:12]2[CH:13]=[C:14]([Br:17])[CH:15]=[C:16]3[C:11]=2[CH2:10][C:9](=[O:38])[NH:8]3)[C:20]1=[O:37])[CH2:29][CH2:30][CH3:31]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67360592HCID 67360592, compound

Product 1

HCID 67360730Methyl 3-[(6-bromo-2,3-dihydro-2-oxo-1H-indol-4-yl)methyl]-2,3-dihydro-2-oxo-β-propyl-1H-benzimidazole-1-propanoateYield 46.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

6-Bromo-2-tert-butoxycarbonyloxy-4-[3-(1-methoxycarbonylmethyl-butyl)-2-oxo-2,3-dihydro-benzoimidazol-1-ylmethyl]-indole-1-carboxylic acid tert-butyl ester (200 mg, 0.28 mmol) is dissolved in dichloromethane (5 mL) and then trifluoroacetic acid is added (2 mL). The reaction is stirred for 1 hour then evaporated in vacuo to give an oil that is purified by preparative reverse phase LC to give the title compound (63 mg 0.13 mmol 44%). LCMS (ESMS): m/z 487.6 (M+H+).

Workup

  1. customthen evaporated in vacuo
  2. customto give an oil that
  3. customis purified by preparative reverse phase LC

Sources & evidence

ORD record
ord-7585f764c49248f3837516f270dc23d4
Source dataset
uspto-grants-2015_10
Patent number
US09150556B2

Reaction notes

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