HCID 59214162, compound → HCID 86645556, compound

HRID 2361485Notes

Reaction equation

HRID 2361485 reaction equation
Br[C:2]1[N:6]([CH2:7][CH2:8][O:9][CH2:10][CH2:11][O:12][CH2:13][CH2:14][F:15])[C:5]2[CH:16]=[CH:17][CH:18]=[CH:19][C:4]=2[N:3]=1.[CH3:20][N:21]([C:29]1[CH:34]=[CH:33][C:32]([C:35]#[CH:36])=[CH:31][CH:30]=1)[C:22](=[O:28])[O:23][C:24]([CH3:27])([CH3:26])[CH3:25]>>[F:15][CH2:14][CH2:13][O:12][CH2:11][CH2:10][O:9][CH2:8][CH2:7][N:6]1[C:5]2[CH:16]=[CH:17][CH:18]=[CH:19][C:4]=2[N:3]=[C:2]1[C:36]#[C:35][C:32]1[CH:31]=[CH:30][C:29]([N:21]([CH3:20])[C:22](=[O:28])[O:23][C:24]([CH3:25])([CH3:27])[CH3:26])=[CH:34][CH:33]=1

Participants

3

Reactant 2

HCID 59214162HCID 59214162, compoundHCID 86645557HCID 86645557, compound2×

Product 1

HCID 86645556HCID 86645556, compoundYield 19.21%

Procedure

T541 was prepared using general procedure B from 2-bromo-1-(2-(2-(2-fluoroethoxy)ethoxy)ethyl)-1H-benzo[d]imidazole and tert-butyl methyl-4-(ethynyl)phenylcarbamate. Reaction was performed on a 72 mgs scale of 2-bromo-1-(2-(2-(2-fluoroethoxy)ethoxy)ethyl)-1H-benzo[d]imidazole. The crude product was purified by ISCO column to afford tert-butyl 4-((1-(2-(2-(2-fluoroethoxy)ethoxy)ethyl)-1H-benzo[d]imidazol-2-yl)ethynyl)phenyl(methyl)carbamate (0.02 g, 19.21%). It was then dissolved in acetonitrile (1.0 mL). To this solution was added 20% Sulfuric acid (1.0 mL, 3.75 mmol). The reaction mixture was stirred at room temperature for 30 mins. The crude product was purified by prep HPLC to afford T541 TFA salt (0.004 g, 19.44%). 1H NMR (400 MHz, CD3CN) δ 7.78-7.76 (m, 1H), 7.70-7.68 (m, 1H), 7.51-7.45 (m, 4H), 6.66-6.64 (m, 2H), 4.63-4.60 (m, 2H), 4.44-4.42 (m, 1H), 4.32-4.30 (m, 1H), 3.95-3.92 (m, 2H), 3.57-3.53 (m, 3H), 3.48-3.45 (m, 3H), 2.82 (m, 3H). MS (ESI): 382.1 (M+H+).

Workup

  1. customT541 was prepared
  2. customReaction
  3. customThe crude product was purified by ISCO column

Sources & evidence

ORD record
ord-3c7e17e5bc494a879a5642e2a917ef2b
Source dataset
uspto-grants-2014_04
Patent number
US08691187B2

Reaction notes

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