1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 70675028, compound

HRID 1522064Notes

Reaction equation

HRID 1522064 reaction equation
[O:1]=[S:2]1(=[O:18])[N:7]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH2:6][CH2:5][CH2:4][N:3]1[CH2:14][C:15]([OH:17])=O.Cl.[CH:20]12[CH2:29][CH:24]3[CH2:25][CH:26]([CH2:28][CH:22]([CH2:23]3)[CH:21]1[NH2:30])[CH2:27]2.CCN=C=NCCCN(C)C>C(Cl)Cl>[CH:20]12[CH2:29][CH:24]3[CH2:25][CH:26]([CH2:28][CH:22]([CH2:23]3)[CH:21]1[NH:30][C:15](=[O:17])[CH2:14][N:3]1[CH2:4][CH2:5][CH2:6][N:7]([C:8]3[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=3)[S:2]1(=[O:1])=[O:18])[CH2:27]2

Participants

5

Reactant 3

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 253312-Aminoadamantane hydrochlorideHCID 70683867HCID 70683867, compound

Product 1

HCID 70675028HCID 70675028, compoundYield 54%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To 2-(1,1-dioxido-6-phenyl-1,2,6-thiadiazinan-2-yl)acetic acid (100 mg, 0.37 mmol) in DCM (5 mL), were added 2-adamantan amine HCl (105 mg, 0.56 mmol), TEA (74.9 mg, 0.74 mmol) and EDCI (212.8 mg, 1.11 mmol). The reaction mixture was agitated for 5 hr at room temperature and extracted using CH2Cl2 and brine. The organic layer was dried over MgSO4. The residue was purified by silica gel column chromatography to give N-(adamantan-2-yl)-(1,1-dioxido-6-phenyl-1,2,6-thiadiazinan-2-yl)acetamide (80 mg, 54%). 1H NMR (300 MHz, CDCl3): δ 7.41-7.26 (m, 5H), 7.02-6.99 (brd, 1H), 4.07 (m, 1H), 3.94 (s, 2H), 3.81-3.74 (m, 4H), 2.03-1.94 (m, 4H), 1.85-1.74 (m, 10H), 1.66-1.60 (m, 3H).

Workup

  1. extractionextracted
  2. dry with materialThe organic layer was dried over MgSO4
  3. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-2ab16c5eacc2484fa8968118a634ea60
Source dataset
uspto-grants-2015_07
Patent number
US09073906B2

Reaction notes

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