Triethylamine → HCID 178456233, compound

HRID 254630Notes

Reaction equation

HRID 254630 reaction equation
C(O[C:5]1([CH2:10][N:11]2[CH:15]=[C:14]([C:16]([CH3:19])([CH3:18])[CH3:17])[S:13]/[C:12]/2=[N:20]\[C:21]([C:23]2[CH:28]=[C:27](Cl)[CH:26]=[CH:25][C:24]=2[O:30][CH3:31])=S)[CH2:9]CCC1)(=O)C.C([N:34]([CH2:37]C)CC)C.[N:39]#[C:40][NH2:41]>C(#N)C.[Hg](OC(C)=O)OC(C)=O>[C:16]([C:14]1[S:13]/[C:12](=[N:20]\[C:21]([C:23]2[CH:28]=[C:27]([C:37]#[N:34])[CH:26]=[CH:25][C:24]=2[O:30][CH3:31])=[N:41][C:40]#[N:39])/[N:11]([CH2:10][CH2:5][CH3:9])[CH:15]=1)([CH3:19])([CH3:17])[CH3:18]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 9864CyanamideHCID 178490713HCID 178490713, compound

Product 1

HCID 178456233HCID 178456233, compoundYield 73.8%

Reagents, catalysts & solvents 2

HCID 16683746DiacetyloxymercuryCatalystHCID 6342AcetonitrileSolvent

Procedure

The product of Example 24D (0.30 g, 0.80 mmol), triethylamine (0.30 mL, 2.2 mmol), cyanamide (70 mg, 1.6 mmol) and Hg(OAc)2 (0.33 g, 1.0 mmol) in acetonitrile (10 mL) were processed as described in Example 16E to provide the title compound (0.23 g, 0.59 mmol, 73% yield). 1H NMR (300 MHz, CDCl3) δ ppm 0.97 (t, J=7.3 Hz, 3H), 1.39 (s, 9H), 1.79-1.92 (m, 2H), 4.00 (s, 3H), 4.17 (dd, J=7.4 Hz, 2H), 6.79 (s, 1H), 7.08 (d, J=8.5 Hz, 1H), 7.64-7.75 (m, 2H); MS (DCI/NH3) m/z 382 (M+H)+. Anal. calculated for C20H23N5OS: C, 62.97; H, 6.08; N, 18.36. Found: C, 62.82; H, 5.91; N, 18.26.

Sources & evidence

ORD record
ord-8ebb92dc6def4894a7edb02416592b45
Source dataset
uspto-grants-2011_01
Patent number
US07875640B2

Reaction notes

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