Trifluoroacetic acid → HCID 178419809, compound

HRID 1471111

Reaction equation

HRID 1471111 reaction equation
C(OC([N:8]1[CH2:12][CH2:11][CH2:10][CH:9]1[C:13]1[NH:17][C:16]2[CH:18]=[C:19]([C:22]3[CH:23]=[C:24]4[C:29](=[CH:30][CH:31]=3)[CH:28]=[C:27]([C:32]3[CH:52]=[CH:51][C:35]5[NH:36][C:37]([CH:39]6[CH2:43][CH2:42][CH2:41][N:40]6C(OC(C)(C)C)=O)=[N:38][C:34]=5[CH:33]=3)[CH:26]=[CH:25]4)[CH:20]=[CH:21][C:15]=2[N:14]=1)=O)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH:28]1[C:29]2[C:24](=[CH:23][C:22]([C:19]3[CH:20]=[CH:21][C:15]4[NH:14][C:13]([CH:9]5[CH2:10][CH2:11][CH2:12][NH:8]5)=[N:17][C:16]=4[CH:18]=3)=[CH:31][CH:30]=2)[CH:25]=[CH:26][C:27]=1[C:32]1[CH:52]=[CH:51][C:35]2[NH:36][C:37]([CH:39]3[CH2:43][CH2:42][CH2:41][NH:40]3)=[N:38][C:34]=2[CH:33]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 178451672HCID 178451672, compound

Product 1

HCID 178419809HCID 178419809, compoundYield 99.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of tert-butyl 2-(5-(6-(2-(1-(tert-butoxycarbonyl)-2-pyrrolidinyl)-1H-benzimidazol-6-yl)-2-naphthyl)-1H-benzimidazol-2-yl)-1-pyrrolidinecarboxylate (591 mg. 0.844 mmol) and TFA (2 mL) in CH2Cl2 (10 mL) was stirred at ambient conditions for 2 hours. The volatile component was removed in vacuo and the resulting material was loaded onto a MCX column, flushed with methanol, released with 2.0 M NH3/methanol elution) and concentrated to provide 5,5′-(2,6-naphthalenediyl)bis(2-(2-pyrrolidinyl)-1H-benzimidazole) (419 mg) as tan solid. LC-MS retention time 1.02 min; Calcd. for C33H31N5: 498.25 Found m/z 499.25 [M+H]+. LC data was recorded on a Shimadzu LC-10AS liquid chromatograph equipped with a Waters Sunfire 5u C18 4.6×50 mm column using a SPD-10AV UV-Vis detector at a detector wave length of 220 nM. The elution conditions employed a flow rate of 4 mL/min, a gradient of 100% Solvent A/0% Solvent B to 0% Solvent A/100% Solvent B, a gradient time of 3 min, a hold time of 1 min and an analysis time of 4 min where Solvent A was 10% acetonitrile/90% water/0.1% TFA and Solvent B was 90% acetonitrile/10% water/0.1% TFA. 1H NMR (500 MHz, MeOD) δ ppm 8.18 (s, 1H), 8.06 (d, J=8.6 Hz, 1H), 8.00 (s, 1H), 7.84-7.92 (m, 1H), 7.73-7.81 (m, 2H), 5.08 (t, J=7.6 Hz, 1H), 3.56-3.66 (m, 1H), 3.48-3.56 (m, 1H), 2.62-2.71 (m, 1H), 2.36-2.47 (m, 1H), 2.19-2.36 (m, 2H).

Workup

  1. customThe volatile component was removed in vacuo
  2. customflushed with methanol
  3. washreleased with 2.0 M NH3/methanol elution) and
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-68034fc55bf14bfead492d06d6727002
Source dataset
uspto-grants-2015_04
Patent number
US09006455B2

Linked notes

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