Trifluoroacetic acid → HCID 117842915, compound

HRID 2209083Notes

Reaction equation

HRID 2209083 reaction equation
[C:1](O)([C:3](F)(F)F)=[O:2].[CH:8]1([N:11]2[C:15]3[C:16]([O:32][C@@H:33]([C@H:35]4[CH2:39][NH:38][C:37](=[O:40])[CH2:36]4)[CH3:34])=[CH:17][C:18]([C:20]4[CH:25]=[CH:24][C:23]([N:26]5[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]5)=[CH:22][N:21]=4)=[CH:19][C:14]=3[N:13]=[CH:12]2)[CH2:10][CH2:9]1.C(OC(=O)C)(=O)C>C(Cl)Cl>[C:1]([N:29]1[CH2:28][CH2:27][N:26]([C:23]2[CH:24]=[CH:25][C:20]([C:18]3[CH:17]=[C:16]([O:32][C@@H:33]([C@H:35]4[CH2:39][NH:38][C:37](=[O:40])[CH2:36]4)[CH3:34])[C:15]4[N:11]([CH:8]5[CH2:9][CH2:10]5)[CH:12]=[N:13][C:14]=4[CH:19]=3)=[N:21][CH:22]=2)[CH2:31][CH2:30]1)(=[O:2])[CH3:3]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 7918Acetic AnhydrideHCID 117843316HCID 117843316, compound

Product 1

HCID 117842915HCID 117842915, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To the TFA salt of (R)-4-((R)-1-((1-cyclopropyl-5-(5-(piperazin-1-yl)pyridin-2-yl)-1H-benzo[d]imidazol-7-yl)oxy)ethyl)pyrrolidin-2-one: (45 mg, 0.1 mmol) in DCM (1 mL) and TEA (0.07 mL, 0.5 mmol) was added acetic anhydride (0.014 mL, 0.15 mmol). The reaction was stirred at rt for 2 h. The mixture was then concentrated and purified by prep-HPLC (MeCN:water gradient; TFA modified) to give (R)-4-((R)-1-((5-(5-(4-acetylpiperazin-1-yl)pyridin-2-yl)-1-cyclopropyl-1H-benzo[d]imidazol-7-yl)oxy)ethyl)pyrrolidin-2-one: 3.59 as a TFA salt. The salt was then converted to the free base by treatment with MP carbonate resin.

Workup

  1. concentrationThe mixture was then concentrated
  2. custompurified by prep-HPLC (MeCN:water gradient; TFA modified)

Sources & evidence

ORD record
ord-497a152cdcff4d529e60436ca40f4e87
Source dataset
uspto-grants-2016_06
Patent number
US09376441B2

Reaction notes

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