1,2-Dichloroethane → 4-(2-(4-Methyl-1,1-dioxido-6-(2,4,6-trichlorophenyl)-1,2,6-thiadiazinan-2-yl)acetamido)adamantan-1-carboxamide

HRID 1522068Notes

Reaction equation

HRID 1522068 reaction equation
Cl.[NH2:2][CH:3]1[CH:10]2[CH2:11][C:6]3([C:13]([NH2:15])=[O:14])[CH2:7][CH:8]([CH2:12][CH:4]1[CH2:5]3)[CH2:9]2.CCN(C(C)C)C(C)C.[CH3:25][CH:26]1[CH2:31][N:30]([C:32]2[C:37]([Cl:38])=[CH:36][C:35]([Cl:39])=[CH:34][C:33]=2[Cl:40])[S:29](=[O:42])(=[O:41])[N:28]([CH2:43][C:44](O)=[O:45])[CH2:27]1.C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1>CS(C)=O.O>[CH3:25][CH:26]1[CH2:31][N:30]([C:32]2[C:37]([Cl:38])=[CH:36][C:35]([Cl:39])=[CH:34][C:33]=2[Cl:40])[S:29](=[O:42])(=[O:41])[N:28]([CH2:43][C:44]([NH:2][CH:3]2[CH:10]3[CH2:11][C:6]4([C:13]([NH2:15])=[O:14])[CH2:7][CH:8]([CH2:12][CH:4]2[CH2:5]4)[CH2:9]3)=[O:45])[CH2:27]1

Participants

8

Reactant 5

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 66863440HCID 66863440, compoundHCID 867089162-(4-Methyl-1,1-dioxido-6-(2,4,6-trichlorophenyl)-1,2,6-thiadiazinan-2-yl)acetic acid

Product 1

HCID 706751474-(2-(4-Methyl-1,1-dioxido-6-(2,4,6-trichlorophenyl)-1,2,6-thiadiazinan-2-yl)acetamido)adamantan-1-carboxamideYield 64%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

To 4-aminoadamantan-1-carboxamide hydrochloride (900 mg, 3.9 mmol) in DMSO (40 mL) and i-prOH (50 mL), were added DIPEA (2.5 g, 19.5 mmol), 2-(4-methyl-1,1-dioxido-6-(2,4,6-trichlorophenyl)-1,2,6-thiadiazinan-2-yl)acetic acid (1.8 g, 4.7 mmol), EDC (894 mg, 4.7 mmol) and HOBT (632 mg, 4.7 mmol), and then agitated for 5 hr at room temperature. After the addition of water, the resultant extracted with EtOAc, dried (Na2SO4), filtered and concentrated under reduced pressure, followed by column chromatography (MeOH/DCM 5%), finally giving the title compound (solid, 980 mg, y=64%) E-form. 1H NMR (300 MHz, DMSO-d6) δ 7.41 (d, J=2.4 Hz, 1H), 7.39 (d, J=2.4 Hz, 1H), 5.58 (s, 1H), 5.35 (s, 1H), 4.35 (d, J=17 Hz, 1H), 4.08-4.00 (m, 2H), 3.91-3.85 (m, 1H), 3.73 (d, J=17 Hz, 1H), 3.30-3.17 (m, 2H), 2.70-2.54 (m, 1H), 2.17-1.54 (m, 13H); LC/MS MH+ 563

Workup

  1. extractionthe resultant extracted with EtOAc
  2. dry with materialdried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-f66ee4c0c2044005bd9e2a5b79c2ccce
Source dataset
uspto-grants-2015_07
Patent number
US09073906B2

Reaction notes

Loading…