Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Thiourea | HCID 2723790 | — |
| Reactant | HCID 89501297 | HCID 89501297 | — |
| Solvent | Ethanol | HCID 702 | — |
| Product | HCID 117777552 | HCID 117777552 | 14.7% |
Reaction Steps
To a solution of N-(5-(5-(2-bromoacetyl)-1H-benzo[d]imidazol-1-yl)-2′,4′-difluoro-[1,1′-biphenyl]-3-yl)acetamide (100 mg, 0.20 mmol) in ethanol was added thiourea (20 mg, 0.30 mmol, 1.5 eq). The mixture was stirred at 60° C. for 3 h. The mixture was quenched and extracted as in Example 1(d). The solvent was distilled off to give the crude residue which was purified by preparative HPLC to give the product in 14.7% yield (14 mg). 1H NMR (300 MHz, CD3OD): δ 8.73 (s, 1H), 8.11 (s, 1H), 8.01 (s, 1H), 7.73-7.69 (m, 2H), 7.62-7.50 (m, 2H), 7.45 (d, 1H), 7.10-6.99 (m, 3H), 2.10 (s, 3H); LC-MS (ESI): Calculated mass: 461.4; Observed mass: 462.1 [M+H]+ (rt: 0.80 min).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09447091B2 |
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| Source dataset | uspto-grants-2016_09 |
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| ORD ID | ord-139f855e69c94e98adac2926e277258c |
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| Source note | uspto-grants-2016_09 |
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