Trifluoroacetic acid → HCID 117843316, compound

HRID 2209082Notes

Reaction equation

HRID 2209082 reaction equation
[CH:1]1([N:4]2[C:8]3[C:9]([O:32][C@@H:33]([C@@H:35]4[CH2:39][C:38](=[O:40])[N:37]([C@@H](C5C=CC(OC)=CC=5)C)[CH2:36]4)[CH3:34])=[CH:10][C:11]([C:13]4[N:18]=[CH:17][C:16]([N:19]5[CH2:24][CH2:23][N:22](C(OC(C)(C)C)=O)[CH2:21][CH2:20]5)=[CH:15][CH:14]=4)=[CH:12][C:7]=3[N:6]=[CH:5]2)[CH2:3][CH2:2]1.C(O)(C(F)(F)F)=O>>[CH:1]1([N:4]2[C:8]3[C:9]([O:32][C@@H:33]([C@H:35]4[CH2:36][NH:37][C:38](=[O:40])[CH2:39]4)[CH3:34])=[CH:10][C:11]([C:13]4[CH:14]=[CH:15][C:16]([N:19]5[CH2:20][CH2:21][NH:22][CH2:23][CH2:24]5)=[CH:17][N:18]=4)=[CH:12][C:7]=3[N:6]=[CH:5]2)[CH2:2][CH2:3]1

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 117842994HCID 117842994, compound

Product 1

HCID 117843316HCID 117843316, compound

Procedure

tert-butyl 4-(6-(1-cyclopropyl-7-((R)-1-((R)-1-((R)-1-(4-methoxyphenyl)ethyl)-5-oxopyrrolidin-3-yl)ethoxy)-1H-benzo[d]imidazol-5-yl)pyridin-3-yl)piperazine-1-carboxylate (129 mg, 0.189 mmol) was treated with TFA (3 mL) at 60° C. for 14 h. The reaction mixture was then concentrated to give (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: 3.58 as a TFA salt which was used further without purification. LCMS-ESI+ (m/z): [M+H]+ calcd for C25H31N6O2: 447.3; found 447.2.

Workup

  1. concentrationThe reaction mixture was then concentrated

Sources & evidence

ORD record
ord-2b00e75d92f94ffc88b25b4a672ed852
Source dataset
uspto-grants-2016_06
Patent number
US09376441B2

Reaction notes

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