Trifluoroacetic acid → HCID 58315880, compound

HRID 625558Notes

Reaction equation

HRID 625558 reaction equation
C(OC([N:8]1[CH2:12][CH2:11][CH2:10][C@H: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[NH:36][C:35]([C@@H:37]5[CH2:41][CH2:40][CH2:39][N:38]5C(OC(C)(C)C)=O)=[N:34][CH:33]=3)[CH:26]=[CH:25]4)[CH:20]=[CH:21][C:15]=2[N:14]=1)=O)(C)(C)C.C(OC(N1CCC[C@H]1C1NC2C=C(C3C=C4C(C=CC(C5NC([C@@H]6CCCN6C(OC(C)(C)C)=O)=NC=5)=C4)=CC=3)C=CC=2N=1)=O)(C)(C)C.[C:97]([OH:103])([C:99]([F:102])([F:101])[F:100])=[O:98]>C(Cl)Cl>[C:97]([OH:103])([C:99]([F:102])([F:101])[F:100])=[O:98].[NH:8]1[CH2:12][CH2:11][CH2:10][C@H:9]1[C:13]1[NH:17][C:16]2[CH:18]=[C:19]([C:22]3[CH:31]=[CH:30][C:29]4[C:24](=[CH:25][CH:26]=[C:27]([C:32]5[NH:36][C:35]([C@@H:37]6[CH2:41][CH2:40][CH2:39][NH:38]6)=[N:34][CH:33]=5)[CH:28]=4)[CH:23]=3)[CH:20]=[CH:21][C:15]=2[N:14]=1

Participants

6

Reactant 3

HCID 6422Trifluoroacetic acid2×HCID 58316112HCID 58316112, compoundHCID 66982164HCID 66982164, compound

Product 2

HCID 6422Trifluoroacetic acidHCID 58315880HCID 58315880, compoundYield 31%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of (S)-tert-butyl 2-(5-(6-(2-((S)-1-(tert-butoxycarbonyl)pyrrolidin-2-yl)-1H-benzo[d]imidazol-6-yl)naphthalen-2-yl)-1H-imidazol-2-yl)pyrrolidine-1-carboxylate and (S)-tert-butyl 2-(5-(7-(2-((S)-1-(tert-butoxycarbonyl)pyrrolidin-2-yl)-1H-benzo[d]imidazol-6-yl)naphthalen-2-yl)-1H-imidazol-2-yl)pyrrolidine-1-carboxylate as TFA salts (74 mg) and TFA (2 mL) in CH2Cl2 (10 mL) was stirred at ambient conditions for 4 hours. The volatile component was removed in vacuo. The crude material was purified by a reverse phase HPLC (0 to 50% water/acetonitrile/TFA) to provide a TFA salt of 2-((S)-pyrrolidin-2-yl)-6-(6-(2-((S)-pyrrolidin-2-yl)-1H-imidazol-5-yl)naphthalen-2-yl)-1H-benzo[d]imidazole (32 mg, 31%) as yellow oil and a TFA salt of 2-((S)-pyrrolidin-2-yl)-6-(7-(2-((S)-pyrrolidin-2-yl)-1H-imidazol-4-yl)naphthalen-2-yl)-1H-benzo[d]imidazole (16 mg) as yellow oil.

Workup

  1. customThe volatile component was removed in vacuo
  2. customThe crude material was purified by a reverse phase HPLC (0 to 50% water/acetonitrile/TFA)

Sources & evidence

ORD record
ord-e938927b72064553a1792ece6d33a51a
Source dataset
uspto-grants-2016_04
Patent number
US09303007B2

Reaction notes

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