Triethylamine → HCID 59853604, compound

HRID 731309Notes

Reaction equation

[CH2:1]([O:3][C:4](=[O:17])[CH2:5][C:6]1[NH:11][C:10]2[CH:12]=[CH:13][C:14]([NH2:16])=[CH:15][C:9]=2[S:8][CH:7]=1)[CH3:2].C(N(CC)CC)C.[CH3:25][S:26](Cl)(=[O:28])=[O:27]>ClCCl>[CH2:1]([O:3][C:4](=[O:17])[CH2:5][C:6]1[NH:11][C:10]2[CH:12]=[CH:13][C:14]([NH:16][S:26]([CH3:25])(=[O:28])=[O:27])=[CH:15][C:9]=2[S:8][CH:7]=1)[CH3:2]

Participants

Conditions

Temperature: 0 °C

Procedure

A solution of (7-amino-4H-benzo[1,4]thiazin-3-yl)-acetic acid ethyl ester (2.38 g, 9.51 mmol) in dichloromethane (80 mL) was cooled to 0° C. and treated with triethylamine (3.1 g, 30.4 mmol) followed by dropwise addition of methanesulfonyl chloride (1.37 g, 9.51 mmol). The reaction mixture was stirred at 0° C. for 0.5 h and allowed to warm to 25° C. The reaction mixture was concentrated in vacuo and purified by flash column chromatography (Merck silica gel 60, 40-63 μm, ethyl acetate/hexanes) to afford the desired product, (7-methanesulfonylamino-4H-benzo[1,4]thiazin-3-yl)-acetic acid ethyl ester (2.2 g, 6.7 mmol, 71%) as a light tan solid. 1H NMR (400 MHz, CDCl3) δ 1.31 (t, 3H, J=7.0 Hz), 3.00 (s, 3H), 3.43 (s, 2H), 4.19 (quartet, 2H, J=7.1 Hz), 4.73 (s, 1H), 6.28 (s, 1H), 6.85 (d, 1H, J=8.5 Hz), 6.99 (dd, 1H, J1=8.5 Hz, J2=2.4 Hz), 7.12 (d, 1H, J=2.3 Hz), 10.64 (bs, 1H). LC-MS (ESI) calcd for C13H16N2O4S [M+H+] 329.06, found 329.10 [M+H+].

Workup

temperatureto warm to 25° C
concentrationThe reaction mixture was concentrated in vacuo
custompurified by flash column chromatography (Merck silica gel 60, 40-63 μm, ethyl acetate/hexanes)

Sources & evidence

ORD record: ord-bb5151bb4cd746aeba4525d2d58325a9
Source dataset: uspto-grants-2009_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07582626B2

Reaction notes

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