1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 70675029, compound

HRID 1522057Notes

Reaction equation

HRID 1522057 reaction equation
[C:1]([O:5][C:6]([N:8]1[S:13](=[O:15])(=[O:14])[N:12]([CH2:16][C:17]([OH:19])=O)[CH2:11][CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl.[CH:21]12[CH2:30][CH:25]3[CH2:26][CH:27]([CH2:29][CH:23]([CH2:24]3)[CH:22]1[NH2:31])[CH2:28]2.CCN=C=NCCCN(C)C>C(Cl)Cl>[CH:21]12[CH2:30][CH:25]3[CH2:26][CH:27]([CH2:29][CH:23]([CH2:24]3)[CH:22]1[NH:31][C:17](=[O:19])[CH2:16][N:12]1[S:13](=[O:14])(=[O:15])[N:8]([C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7])[CH2:9][CH2:10][CH2:11]1)[CH2:28]2

Participants

5

Reactant 3

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 253312-Aminoadamantane hydrochlorideHCID 86708908HCID 86708908, compound

Product 1

HCID 70675029HCID 70675029, compoundYield 35%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-(6-(tert-butoxycarbonyl)-1,1-dioxido-1,2,6-thiadiazinan-2-yl)acetic acid (60 mg, 0.204 mmol) in CH2Cl2 (5 mL), were added 2-adamantan amine HCl (57.5 mg, 0.306 mmol), TEA (41.3 mg, 0.408 mmol) and EDCI (117.3 mg, 0.612 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 tert-butyl 6-(2-(adamantan-2-yl amino)-2-oxoethyl)-1,2,6-thiadiazinan-2-carboxylate 1,1-dioxide (5.30 mg, 35%). 1H NMR (300 MHz, CDCl3): δ 6.90 (brd, 1H), 4.06 (m, 1H), 4.00 (t, J=5.8 Hz, 2H), 3.83 (s, 2H), 3.66 (t, J=5.8 Hz, 2H), 1.92-1.63 (m, 15H), 1.52 (s, 9H).

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-2649a593e8754c7385fea5f46a69a89c
Source dataset
uspto-grants-2015_07
Patent number
US09073906B2

Reaction notes

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