2-Acetamido-4-methylthiazole-5-sulfonyl chloride → HCID 58838513, compound

HRID 2374453Notes

Reaction equation

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

Participants

Conditions

Temperature: 24 °C

Procedure

To a solution of tert-butyl (6-amino-4-methylpyridin-2-yl)carbamate (1.2 g, 6.0 mmol) in pyridine (30 mL) was added 2-acetamido-4-methyl-5-thiazolesulfonyl chloride (1.5 g, 6.0 mmol). The resulting mixture was stirred at 24° C. for 16 hours. The reaction was concentrated in vacuo (˜25 mm Hg). Purification by high performance flash chromatography (0→5% methanol in dichloromethane) provided the intermediate (2.1 g, 80%). 1H NMR (400 MHz, CDCl3), δ: 7.43 (br s, 1H), 6.99 (s, 1H), 5.31 (s, 1H) 2.34 (s, 3H), 2.31 (s, 3H), 2.22 (s, 3H), 1.54 (s, 9H); LRMS (ESI) m/z: 342 [M-CO2C(CH3)3]+.

Workup

concentrationThe reaction was concentrated in vacuo (˜25 mm Hg)
customPurification by high performance flash chromatography (0→5% methanol in dichloromethane)

Sources & evidence

ORD record: ord-42dfedeb5ac34e33b8ad8ba1929c00d7
Source dataset: uspto-grants-2008_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07462634B2

Reaction notes

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