Tetrabutylammonium Fluoride → Methyl 1-((1-(3-(1H-pyrazol-5-yl)benzyl)-5-(quinolin-2-ylmethoxy)-1H-benzo[d]imidazol-2-yl)methyl)cyclopentanecarboxylate

HRID 2178476Notes

Reaction equation

[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[CH2:11][O:12][C:13]1[CH:51]=[CH:50][C:16]2[N:17]([CH2:30][C:31]3[CH:36]=[CH:35][CH:34]=[C:33]([C:37]4[N:41](COCC[Si](C)(C)C)[N:40]=[CH:39][CH:38]=4)[CH:32]=3)[C:18]([CH2:20][C:21]3([C:26]([O:28][CH3:29])=[O:27])[CH2:25][CH2:24][CH2:23][CH2:22]3)=[N:19][C:15]=2[CH:14]=1.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1>[NH:41]1[C:37]([C:33]2[CH:32]=[C:31]([CH:36]=[CH:35][CH:34]=2)[CH2:30][N:17]2[C:16]3[CH:50]=[CH:51][C:13]([O:12][CH2:11][C:2]4[CH:3]=[CH:4][C:5]5[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=5)[N:1]=4)=[CH:14][C:15]=3[N:19]=[C:18]2[CH2:20][C:21]2([C:26]([O:28][CH3:29])=[O:27])[CH2:25][CH2:24][CH2:23][CH2:22]2)=[CH:38][CH:39]=[N:40]1

Participants

Conditions

Temperature: 70 °C

Procedure

To a 20 mL vial was added methyl 1-((5-(quinolin-2-ylmethoxy)-1-(3-(1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrazol-5-yl)benzyl)-1H-benzo[d]imidazol-2-yl)methyl)cyclopentanecarboxylate (51 mg, 0.08 mmol) and THF (2 mL) followed by treatment with TBAF (0.4 mL, 1 M). The reaction mixture was heated to 70° C. After 24 hours the mixture was cooled to RT and concentrated to dryness. The residue was purified using FCC to provide the title compound. MS (ESI): mass calcd. for C35H33N5O3, 571.68; m/z found 572.2 [M+H]+.

Workup

temperatureAfter 24 hours the mixture was cooled to RT
concentrationconcentrated to dryness
customThe residue was purified

Sources & evidence

ORD record: ord-c24a0d35fda14791a6109acdc55cfb6a
Source dataset: uspto-grants-2015_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09067917B2

Reaction notes

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