Pyridine → HCID 15231549, compound

HRID 1081483Notes

Reaction equation

[CH2:1]([O:3][C:4]1[CH:31]=[CH:30][C:7]2[N:8]([S:18]([C:21]3[CH:26]=[CH:25][C:24]([NH2:27])=[CH:23][C:22]=3[O:28][CH3:29])(=[O:20])=[O:19])[C:9](=[O:17])[N:10]([CH:11]3[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]3)[C:6]=2[CH:5]=1)[CH3:2].N1C=CC=CC=1.[Cl:38][CH2:39][C:40](Cl)=[O:41]>C(Cl)Cl>[CH2:1]([O:3][C:4]1[CH:31]=[CH:30][C:7]2[N:8]([S:18]([C:21]3[CH:26]=[CH:25][C:24]([NH:27][C:40](=[O:41])[CH2:39][Cl:38])=[CH:23][C:22]=3[O:28][CH3:29])(=[O:19])=[O:20])[C:9](=[O:17])[N:10]([CH:11]3[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]3)[C:6]=2[CH:5]=1)[CH3:2]

Participants

Conditions

Temperature: 20 °C

Procedure

0.52 g of the compound obtained in Example 5 step B), 25 ml of DCM and 0.5 g of pyridine were mixed. 0.54 ml of chloroacetyl chloride in 10 ml of DCM was then added over 5 minutes at 20° C. The reaction mixture was stirred for 2 hours at 20° C. and then concentrated under vacuum at 20° C. The residue was extracted with AcOEt and washed with water, then with 1N hydrochloric acid and then with water. It was dried over sodium sulfate and the solvent was evaporated off to give the expected product, which crystallized from isopropyl ether. m=0.6 g. M.p.=232° C.

Workup

concentrationconcentrated under vacuum at 20° C
extractionThe residue was extracted with AcOEt
washwashed with water
dry with materialIt was dried over sodium sulfate
customthe solvent was evaporated off

Sources & evidence

ORD record: ord-7d8ab79458c64a128ff7a27d7cb75e6a
Source dataset: uspto-grants-1996_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05585394

Reaction notes

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