Pyridine → Methyl 1-((1-(3-cyanobenzyl)-5-(quinolin-2-ylmethoxy)-1H-benzo[d]imidazol-2-yl)methyl)cyclopentanecarboxylate

HRID 1776742Notes

Reaction equation

HRID 1776742 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH:37]=[CH:38][CH:39]=1)[CH2:5][N:6]1[C:10]2[CH:11]=[CH:12][C:13]([O:15][CH2:16][C:17]3[CH:26]=[CH:25][C:24]4[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=4)[N:18]=3)=[CH:14][C:9]=2[N:8]=[C:7]1[CH2:27][C:28]1([C:33]([O:35][CH3:36])=[O:34])[CH2:32][CH2:31][CH2:30][CH2:29]1.[C:40]([Cu])#[N:41].N1C=CC=CC=1>CC(N(C)C)=O>[C:40]([C:2]1[CH:3]=[C:4]([CH:37]=[CH:38][CH:39]=1)[CH2:5][N:6]1[C:10]2[CH:11]=[CH:12][C:13]([O:15][CH2:16][C:17]3[CH:26]=[CH:25][C:24]4[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=4)[N:18]=3)=[CH:14][C:9]=2[N:8]=[C:7]1[CH2:27][C:28]1([C:33]([O:35][CH3:36])=[O:34])[CH2:29][CH2:30][CH2:31][CH2:32]1)#[N:41]

Participants

5

Reactant 3

HCID 1049PyridineHCID 90414509Methyl 1-{[1-(3-bromobenzyl)-5-(quinolin-2-ylmethoxy)-1H-benzimidazol-2-yl]methyl}cyclopentane-carboxylateHCID 178418546HCID 178418546, compound

Product 1

HCID 90414314Methyl 1-((1-(3-cyanobenzyl)-5-(quinolin-2-ylmethoxy)-1H-benzo[d]imidazol-2-yl)methyl)cyclopentanecarboxylateYield 47.1%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

To a 5 mL microwave vial were added methyl 1-{[1-(3-bromobenzyl)-5-(quinolin-2-ylmethoxy)-1H-benzimidazol-2-yl]methyl}cyclopentanecarboxylate (94 mg, 0.16 mmol), CuCN (31 mg, 0.34 mmol), pyridine (0.5 mL) and DMA (1.5 mL). The vial was flushed with N2, then capped and irradiated in the microwave at 200° C. for 4 h. The resulting mixture was cooled to RT, poured into water (10 mL) and extracted with EtOAc. The organics were concentrated to dryness and the resulting residue was purified by FCC to provide 40 mg of the title compound. MS (ESI): mass calcd. for C33H30N4O3, 530.63; m/z found, 531.2 [M+H]+.

Workup

  1. customThe vial was flushed with N2
  2. customcapped
  3. customirradiated in the microwave at 200° C. for 4 h
  4. additionpoured into water (10 mL)
  5. extractionextracted with EtOAc
  6. concentrationThe organics were concentrated to dryness
  7. customthe resulting residue was purified by FCC

Sources & evidence

ORD record
ord-32cc801ef4e9489a87c9af18b4c8e662
Source dataset
uspto-grants-2016_02
Patent number
US09265770B2

Reaction notes

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