Triethylamine → HCID 178490588, compound

HRID 538775Notes

Reaction equation

HRID 538775 reaction equation
[C:1]([O:4][C:5]1([CH2:9][N:10]2[CH:14]=[C:13]([C:15]([CH3:18])([CH3:17])[CH3:16])[S:12]/[C:11]/2=[N:19]\[C:20]([C:22]2[CH:27]=[C:26]([C:28]([F:31])([F:30])[F:29])[CH:25]=[CH:24][C:23]=2[O:32][CH3:33])=S)[CH2:8][CH2:7][CH2:6]1)(=[O:3])[CH3:2].C(N(CC)CC)C.[N:41]#[C:42][NH2:43]>C(#N)C.[Hg](OC(C)=O)OC(C)=O>[C:1]([O:4][C:5]1([CH2:9][N:10]2[CH:14]=[C:13]([C:15]([CH3:18])([CH3:17])[CH3:16])[S:12]/[C:11]/2=[N:19]\[C:20](=[N:43][C:42]#[N:41])[C:22]2[CH:27]=[C:26]([C:28]([F:31])([F:30])[F:29])[CH:25]=[CH:24][C:23]=2[O:32][CH3:33])[CH2:8][CH2:7][CH2:6]1)(=[O:3])[CH3:2]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 9864CyanamideHCID 178490591HCID 178490591, compound

Product 1

HCID 178490588HCID 178490588, compoundYield 89.5%

Reagents, catalysts & solvents 2

HCID 16683746DiacetyloxymercuryCatalystHCID 6342AcetonitrileSolvent

Procedure

The product of Example 34C (0.97 g, 1.9 mmol), triethylamine (1.1 mL, 7.8 mmol), cyanamide (0.25 g, 5.8 mmol) and Hg(OAc)2 (1.2 g, 3.9 mmol) in acetonitrile (15 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 1.38 (s, 9H), 1.73-1.86 (m, 1H), 1.85-1.98 (m, 1H), 2.01 (s, 3H), 2.21-2.48 (m, 4H), 3.98 (s, 3H), 4.77 (s, 2H), 6.63 (s, 1H), 7.09 (d, J=8.5 Hz, 1H), 7.60-7.71 (m, 2H); MS (DCI/NH3) m/z 509 (M+H)+. Anal. calculated for C24H27F3N4O3S; C, 56.68; H, 5.35; N, 11.02. Found: C, 56.50; H, 5.10; N, 10.67.

Sources & evidence

ORD record
ord-13495c72558949e788fd838c07f4a0d5
Source dataset
uspto-grants-2014_10
Patent number
US08865753B2

Reaction notes

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