Chloroacetyl chloride → HCID 59432898, compound

HRID 1809335Notes

Reaction equation

[S:1]1[CH:5]=[CH:4][N:3]=[C:2]1[NH:6][S:7]([C:10]1[CH:11]=[C:12]2[C:17](=[CH:18][CH:19]=1)[NH:16][CH2:15][CH2:14][CH2:13]2)(=[O:9])=[O:8].CCN(CC)CC.[Cl:27][CH2:28][C:29](Cl)=[O:30]>C(Cl)Cl>[S:1]1[CH:5]=[CH:4][N:3]=[C:2]1[NH:6][S:7]([C:10]1[CH:11]=[C:12]2[C:17](=[CH:18][CH:19]=1)[N:16]([C:29](=[O:30])[CH2:28][Cl:27])[CH2:15][CH2:14][CH2:13]2)(=[O:9])=[O:8]

Participants

Conditions

Temperature: 0 °C

Procedure

Under N2, a solution of 1,2,3,4-Tetrahydro-quinoline-6-sulfonic acid thiazol-2-ylamide (50 mg, 0.17 mmol), Et3N (17 mg, 24 μl, 0.17 mmol) and CH2Cl2 (0.5 mL) was cooled to 0° C. Chloroacetyl chloride (77 mg, 56 μl, 0.68 mmol) was added dropwise, over a period of 10 minutes. This reaction mixture was stirred at 0° C. for 2 hours. The mixture was purified via silica gel chromatography using 2% MeOH in CH2Cl2 to obtain the amide (30 mg, 0.08 mmol, 47% yield). LC/MS (10-99%) M/Z: M+1 obs=372.1; tR=2.51 min.

Workup

customThe mixture was purified via silica gel chromatography

Sources & evidence

ORD record: ord-cde1762a9f274d3ebe25b827816e89d4
Source dataset: uspto-grants-2013_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08362032B2

Reaction notes

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