Trifluoroacetic acid → HCID 178509455, compound

HRID 497928Notes

Reaction equation

[C:1]1([CH2:7][C@H:8]2[N:14]([S:15]([C:18]3[S:19][CH:20]=[CH:21][CH:22]=3)(=[O:17])=[O:16])[CH2:13][C:12]3[CH:23]=[C:24]([C:27]#[N:28])[CH:25]=[CH:26][C:11]=3[NH:10][CH2:9]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[NH:29]1[CH:33]=[C:32]([CH:34]=O)[N:31]=[CH:30]1.FC(F)(F)C(O)=O.FC(F)(F)C(OC(=O)C(F)(F)F)=O.C([SiH](CC)CC)C>C1(C)C=CC=CC=1>[NH:29]1[CH:33]=[C:32]([CH2:34][N:10]2[C:11]3[CH:26]=[CH:25][C:24]([C:27]#[N:28])=[CH:23][C:12]=3[CH2:13][N:14]([S:15]([C:18]3[S:19][CH:20]=[CH:21][CH:22]=3)(=[O:17])=[O:16])[C@H:8]([CH2:7][C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)[CH2:9]2)[N:31]=[CH:30]1

Participants

Conditions

Temperature: 22.5 °C

Procedure

(R)-2,3,4,5-tetrahydro-3-(phenylmethyl)-4-(2-thienylsulfonyl)-1H- 1,4-benzodiazepine-7-carbonitrile (10 g) and imidazole-4-carboxaldehyde (2.6 g) were mixed in toluene (20 mL) at 20 to 25° C. To this stirred slurry, first trifluoroacetic acid (9.4 mL) and then trifluoroacetic acid anhydride (5.2 mL) were added sequentially while maintaining the temperature below 30° C. The biphasic mixture was vigorously stirred at 20 to 25° C. for 2 hours. Triethylsilane was then added and the reaction mixture was stirred at 20 to 25° C. until the reaction was determined to be complete according to HPLC assay. The reaction mixture was polish-filtered, e.g., through filter paper or a celite bed. The solvent was removed by evaporation, and a viscous yellow oil containing approximately 100% yield of the crude title product was collected.

Workup

temperaturewhile maintaining the temperature below 30° C
stirringthe reaction mixture was stirred at 20 to 25° C. until the reaction
filtrationThe reaction mixture was polish-filtered
filtratione.g., through filter paper
customThe solvent was removed by evaporation

Sources & evidence

ORD record: ord-30a5194cb46d441dad499f0601af3734
Source dataset: uspto-grants-2005_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06949642B2

Reaction notes

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