Triethylamine → HCID 178466557, compound

HRID 254635Notes

Reaction equation

HRID 254635 reaction equation
[C:1]([C:5]1[S:9]/[C:8](=[N:10]\[C:11](=S)[C:12]2[CH:17]=[C:16]([C:18]([F:21])([F:20])[F:19])[CH:15]=[CH:14][C:13]=2[O:22][CH2:23][CH3:24])/[N:7]([CH2:26][C@H:27]2[CH2:31][CH2:30][CH2:29][O:28]2)[CH:6]=1)([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.[N:39]#[C:40][NH2:41]>C(#N)C.[Hg](OC(C)=O)OC(C)=O>[C:1]([C:5]1[S:9]/[C:8](=[N:10]\[C:11]([C:12]2[CH:17]=[C:16]([C:18]([F:21])([F:20])[F:19])[CH:15]=[CH:14][C:13]=2[O:22][CH2:23][CH3:24])=[N:41][C:40]#[N:39])/[N:7]([CH2:26][C@H:27]2[CH2:31][CH2:30][CH2:29][O:28]2)[CH:6]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 9864CyanamideHCID 178466559HCID 178466559, compound

Product 1

HCID 178466557HCID 178466557, compoundYield 309.1%

Reagents, catalysts & solvents 2

HCID 16683746DiacetyloxymercuryCatalystHCID 6342AcetonitrileSolvent

Procedure

The product of Example 36C (0.26 g, 0.55 mmol), triethylamine (0.21 mL, 1.5 mmol), cyanamide (50 mg, 1.1 mmol) and Hg(OAc)2 (0.23 g, 0.71 mmol) in acetonitrile (10 mL) were processed as described in Example 16E to provide the title compound (0.84 g, 1.7 mmol, 85% yield). 1H NMR (300 MHz, CDCl3) δ ppm 1.39 (s, 9H), 1.49 (t, J=6.8 Hz, 3H), 1.56-1.66 (m, 1H), 1.77-1.95 (m, 2H), 1.98-2.12 (m, 1H), 3.73-3.89 (m, 2H), 4.13-4.28 (m, 4H), 4.40-4.52 (m, 1H), 7.01 (s, 1H), 7.06 (d, J=8.1 Hz, 1H), 7.58-7.66 (m, 2H); MS (DCI/NH3) m/z 481 (M+H)+. Anal. calculated for C23H27F3N4O2S: C, 57.49; H, 5.66; N, 11.66. Found: C, 57.38; H, 5.59; N, 11.60.

Sources & evidence

ORD record
ord-cc2ffa989a8f40c6adc763fddbba1702
Source dataset
uspto-grants-2011_01
Patent number
US07875640B2

Reaction notes

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