Cyanamide → HCID 73332470, compound

HRID 1911970Notes

Reaction equation

HRID 1911970 reaction equation
[N:1]#[C:2][NH2:3].[CH3:4][N:5]([C:12]1[S:13][C:14]([C:17]2[CH:18]=[N:19][CH:20]=[CH:21][CH:22]=2)=[N:15][N:16]=1)[C:6](=[O:11])[CH2:7][CH2:8]SC.C(O)(=O)C.C(O)(=O)C.IC1C=CC=CC=1>C1COCC1>[C:2]([NH:3][CH2:8][CH2:7][C:6]([N:5]([CH3:4])[C:12]1[S:13][C:14]([C:17]2[CH:18]=[N:19][CH:20]=[CH:21][CH:22]=2)=[N:15][N:16]=1)=[O:11])#[N:1]

Participants

5

Reactant 3

HCID 9864CyanamideHCID 12217721Iodo benzene diacetateHCID 66613348HCID 66613348, compound

Product 1

HCID 73332470HCID 73332470, compoundYield 29.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-10 °C

Procedure

Cyanamide (42 mg, 1.0 mmol) and N-methyl-3-methylsulfanyl-N-[5-(3-pyridyl)-1,3,4-thiadiazol-2-yl]propanamide (294 mg, 1.0 mmol) were suspended in THF and cooled in a −10° C. bath. Iodobenzene diacetate (322 mg, 1.0 mmol) was added and the resulting suspension was stirred at for 4 h. The reaction mixture was concentrated under reduced pressure and purified by reversed phase silica chromatography eluting with an aqueous acetonitrile mobile phase to yield a white solid (84 mg, 29%): mp 155-159° C.; 1H NMR (300 MHz, CDCl3) δ 9.15 (m, 1H), 8.72 (m, 1H), 8.35 (m, 1H), 7.45 (m, 1H), 4.70 (bs, 1H), 3.90 (s, 3H), 3.55 (m, 2H), 3.05 (m, 2H); ESIMS m/z 289 ([M+H]+).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. custompurified by reversed phase silica chromatography
  3. washeluting with an aqueous acetonitrile mobile phase

Sources & evidence

ORD record
ord-0b59e4a599ec4759a7bca3b1d788dbbc
Source dataset
uspto-grants-2013_12
Patent number
US08604211B2

Reaction notes

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