Triphosgene → HCID 89813898, compound

HRID 525386Notes

Reaction equation

Cl[C:2](Cl)([O:4]C(=O)OC(Cl)(Cl)Cl)Cl.[N:13]1[C:22]2[C:17](=[N:18][CH:19]=[CH:20][CH:21]=2)[C:16]([NH2:23])=[CH:15][CH:14]=1.[NH:24]([C:26]1[CH:31]=[C:30]([N:32]2[C@@H:36]([C:37]3[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=3)[C:35]([CH3:44])([CH3:43])[O:34][C:33]2=[O:45])[CH:29]=[CH:28][N:27]=1)[NH2:25]>C(Cl)Cl>[CH3:44][C:35]1([CH3:43])[O:34][C:33](=[O:45])[N:32]([C:30]2[CH:29]=[CH:28][N:27]=[C:26]([NH:24][NH:25][C:2]([NH:23][C:16]3[C:17]4[C:22](=[CH:21][CH:20]=[CH:19][N:18]=4)[N:13]=[CH:14][CH:15]=3)=[O:4])[CH:31]=2)[C@H:36]1[C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a 10 mL round-bottomed flask was added triphosgene (109 mg, 0.369 mmol, commercially available from Sigma-Aldrich, Milwaukee, Wis.) in DCM (1.117 mL). The solution was cooled to 0° C., and 1,5-naphthyridin-4-amine (53.5 mg, 0.369 mmol) was added in one portion. Under argon, TEA (0.466 mL, 3.35 mmol) was then added dropwise. After stirring at room temperature for 15 minutes, (S)-3-(2-hydrazinylpyridin-4-yl)-5,5-dimethyl-4-phenyloxazolidin-2-one (100 mg, 0.335 mmol) in 6 mL of DCM was added to the reaction mixture. After stirring at room temperature overnight, LC-MS indicated good conversion to the desired product. The reaction mixture was concentrated under reduced pressure to give the product as a black solid which was used directly in the next step without further purification. m/z (ESI) 470.1 (M+H)+.

Workup

stirringAfter stirring at room temperature overnight

Sources & evidence

ORD record: ord-b372cbe2db424a938ed7021cfeb92caf
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09340549B2

Reaction notes

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