HCID 58362709, compound → HCID 67300926, compound

HRID 2361484Notes

Reaction equation

HRID 2361484 reaction equation
Br[C:2]1[N:6]([CH2:7][CH2:8][F:9])[C:5]2[CH:10]=[CH:11][CH:12]=[CH:13][C:4]=2[N:3]=1.[CH3:14][N:15]([C:23]1[CH:28]=[CH:27][C:26]([C:29]#[CH:30])=[CH:25][CH:24]=1)[C:16](=[O:22])[O:17][C:18]([CH3:21])([CH3:20])[CH3:19]>>[F:9][CH2:8][CH2:7][N:6]1[C:5]2[CH:10]=[CH:11][CH:12]=[CH:13][C:4]=2[N:3]=[C:2]1[C:30]#[C:29][C:26]1[CH:25]=[CH:24][C:23]([N:15]([CH3:14])[C:16](=[O:22])[O:17][C:18]([CH3:19])([CH3:21])[CH3:20])=[CH:28][CH:27]=1

Participants

3

Reactant 2

HCID 58362709HCID 58362709, compound2×HCID 59214162HCID 59214162, compound

Product 1

HCID 67300926HCID 67300926, compoundYield 35.3%

Procedure

T534 was prepared using general procedure B from 2-bromo-1-(2-fluoroethyl)-1H-benzo[d]imidazole and tert-butyl methyl-4-(ethynyl)phenylcarbamate. Reaction was performed on a 53 mgs scale of 2-bromo-1-(2-fluoroethyl)-1H-benzo[d]imidazole. The crude product was purified by ISCO column to afford tert-butyl 4-((1-(2-fluoroethyl)-1H-benzo[d]imidazol-2-yl)ethynyl)phenyl(methyl)carbamate (0.03 g, 35.3%). It was dissolved in acetonitrile (0.5 mL). To this solution was added a solution of 20% sulfuric acid (1.5 mL, 5.63 mmol). The resulting mixture was stirred at room temperature for 20 minutes, diluted with water (2.0 mL) and purified by preparative HPLC to afford T534 as TFA salt (0.004 g, 12.88%). 1H NMR (400 MHz, CD3CN) δ 7.81-7.79 (m, 1H), 7.67-7.65 (m, 1H), 7.52-7.48 (m, 4H), 6.66-6.64 (m, 2H), 4.95-4.93 (m, 1H), 4.83-4.478 (m, 2H), 4.74-4.73 (m, 1H), 2.82 (s, 3H); MS (ESI): 294.1 (M+H+).

Workup

  1. customT534 was prepared
  2. customReaction
  3. customThe crude product was purified by ISCO column

Sources & evidence

ORD record
ord-e6bb035ac0a44122a6b82b3e73e74aa4
Source dataset
uspto-grants-2014_04
Patent number
US08691187B2

Reaction notes

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