Triethylamine → HCID 178456233, compound

HRID 538771Notes

Reaction equation

HRID 538771 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-5451b837810a4c6d80860093ac7ac9ce
Source dataset
uspto-grants-2014_10
Patent number
US08865753B2

Reaction notes

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