Tetrahydrofuran → HCID 21886481, compound

HRID 723126Notes

Reaction equation

HRID 723126 reaction equation
C(OC(=O)[NH:7][C:8]([C:10]1[S:11][C:12]([S:26][CH3:27])=[C:13]([S:15]([C:18]2[CH:19]=[N:20][C:21](Cl)=[C:22]([Br:24])[CH:23]=2)(=[O:17])=[O:16])[CH:14]=1)=[NH:9])(C)(C)C.[CH3:29][C:30]1[CH:34]=[CH:33][S:32][C:31]=1[CH2:35][NH2:36].C1COCC1.C(Cl)(Cl)Cl.[F:46][C:47]([F:52])([F:51])[C:48]([OH:50])=[O:49]>>[F:46][C:47]([F:52])([F:51])[C:48]([OH:50])=[O:49].[Br:24][C:22]1[CH:23]=[C:18]([S:15]([C:13]2[CH:14]=[C:10]([C:8]([NH2:7])=[NH:9])[S:11][C:12]=2[S:26][CH3:27])(=[O:16])=[O:17])[CH:19]=[N:20][C:21]=1[NH:36][CH2:35][C:31]1[S:32][CH:33]=[CH:34][C:30]=1[CH3:29]

Participants

5

Reactant 4

HCID 8028TetrahydrofuranHCID 2798756(3-Methylthiophen-2-yl)methanamineHCID 19978452Chloroform trifluoroacetic acidHCID 140043501tert-butyl N-[4-[(5-bromo-6-chloro-3-pyridinyl)sulfonyl]-5-methylsulfanylthiophene-2-carboximidoyl]carbamate

Product 1

HCID 21886481HCID 21886481, compound

Conditions

Temperature
70 °C

Procedure

To a vessel containing a stir bar was added {[4-(5-bromo-6-chloro-pyridine-3-sulfonyl)-5-methylsulfanyl-thiophen-2-yl]-imino-methyl}-carbamic acid tert-butyl ester (0.035 g, 0.066 mmol), 3-methylthiophene-2-methylamine (0.016 g, 0.133 mmol), THF [2 mL]. The reaction vessel was sealed and heated to 70° C. for 18 hours, cooled to room temperature and concentrated in vacuo. Chromatography of crude material (10%–25% EtOAC/Hx) yielded the intermediate which was dissolved in a solution of chloroform/trifluoroacetic acid (1/1) [2 mL] and was allowed to stir at room temperature for 2 hours. The reaction was concentrated in vacuo followed by reverse-phase HPLC [acetonitrile/water (0.01% TFA)] to give the title compound. ESI-MS (m/z): Calcd. for C18H18BrN3O2S4: 517.52 (M+H); found 516.9, 518.9.

Workup

  1. additionTo a vessel containing a stir bar
  2. customThe reaction vessel was sealed
  3. temperaturecooled to room temperature
  4. concentrationconcentrated in vacuo
  5. customChromatography of crude material (10%–25% EtOAC/Hx) yielded the intermediate which
  6. concentrationThe reaction was concentrated in vacuo

Sources & evidence

ORD record
ord-abdedf95039c4594b2a77054aae5bb2c
Source dataset
uspto-grants-2006_11
Patent number
US07138530B2

Reaction notes

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