Hydrochloric Acid → HCID 4478930, compound

HRID 1435625Notes

Reaction equation

HRID 1435625 reaction equation
[NH2:1][C:2]1[S:3][CH:4]=[C:5]([CH2:7][C:8]([O:10][CH2:11][CH3:12])=[O:9])[N:6]=1.[N+:13]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[S:22](Cl)(=[O:24])=[O:23])([O-:15])=[O:14].Cl>>[N+:13]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[S:22]([NH:1][C:2]1[S:3][CH:4]=[C:5]([CH2:7][C:8]([O:10][CH2:11][CH3:12])=[O:9])[N:6]=1)(=[O:24])=[O:23])([O-:15])=[O:14]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 155402-Nitrobenzenesulfonyl chlorideHCID 1044544-Thiazoleacetic acid, 2-amino-, ethyl ester

Product 1

HCID 4478930HCID 4478930, compound

Procedure

The title compound was prepared from ethyl 2-amino-4-thiazolylacetate and 2-nitrobenzenesulfonyl chloride as described in the synthetic METHOD B. The reaction mixture was applied on a Hydromatrix column pre-treated with aqueous HCl (0.5 mL, 2 M) and the eluted with DCM. After concentration the material was purified by preparative LCMS and lyophilized to give a white solid (26.6 mg) with purity >90%: 1H-NMR (DMSO-d6) δ 11.40 (s, NH), 8.24 (m, 1H), 7.65 (m, 3H), 6.39 (s, 1H), 4.21 (dd, J=7.2 Hz, J=14.4 Hz, 2H), 3.73 (s, 2H), 1.28 (t, J=7.2 Hz, 3H); HRMS Calcd (found) for C13H13N3O6S2 m/z 371.0246 (371.0248).

Workup

  1. washthe eluted with DCM
  2. concentrationAfter concentration the material
  3. customwas purified by preparative LCMS

Sources & evidence

ORD record
ord-d87729c962624144bd03b0190304117b
Source dataset
uspto-grants-2009_11
Patent number
US07618961B2

Reaction notes

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