1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → 1-Benzyl-N-(9-chloro-3,4-dihydro-2H-1,5-benzodioxepin-7-ylmethyl)-N-isobutyl azetidine-3-carboxamide

HRID 1024497Notes

Reaction equation

HRID 1024497 reaction equation
[Cl:1][C:2]1[C:7]2[O:8][CH2:9][CH2:10][CH2:11][O:12][C:6]=2[CH:5]=[C:4]([CH2:13][NH:14][CH2:15][CH:16]([CH3:18])[CH3:17])[CH:3]=1.[CH2:19]([N:26]1[CH2:29][CH:28]([C:30]([OH:32])=O)[CH2:27]1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.Cl.C(N=C=NCCCN(C)C)C.CC1C=CN=C(N)C=1C>ClCCl.O>[CH2:19]([N:26]1[CH2:27][CH:28]([C:30]([N:14]([CH2:13][C:4]2[CH:3]=[C:2]([Cl:1])[C:7]3[O:8][CH2:9][CH2:10][CH2:11][O:12][C:6]=3[CH:5]=2)[CH2:15][CH:16]([CH3:17])[CH3:18])=[O:32])[CH2:29]1)[C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1

Participants

7

Reactant 4

HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 31613181-Benzylazetidine-3-carboxylic acidHCID 110078842-Amino-3,4-dimethylpyridineHCID 43087680N-(9-chloro-3,4-dihydro-2H-1,5-benzodioxepin-7-ylmethyl)-2-methylpropan-1-amine

Product 1

HCID 580804741-Benzyl-N-(9-chloro-3,4-dihydro-2H-1,5-benzodioxepin-7-ylmethyl)-N-isobutyl azetidine-3-carboxamide

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

40 mg of N-(9-chloro-3,4-dihydro-2H-1,5-benzodioxepin-7-ylmethyl)-2-methylpropan-1-amine was combined with 28 mg of 1-benzyl-azetidine-3-carboxylic acid in 5 ml dichloromethane. 38 mg of 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride and 26 mg of dimethyl aminopyridine were added. The reaction solution was stirred at room temperature overnight. 5 ml of water was added and the mixture was extracted with 5 ml ethyl acetate three times. The organic layer was washed with saturated sodium bicarbonate, water and brine, dried over anhydrous sodium phosphate and concentrated under reduced pressure. The product was purified by column chromatography using 75% ethyl acetate in hexane as a resin: MS (m+1)=443.3; 1H NMR (500 MHz, CDCl3) 0.95 (m, 6H), 1.95 (m, 1H), 2.05 (m, 1H), 2.25 (m, 2H), 2.95 (d, 1H), 3.00 (d, 1H), 3.40 (m, 1H), 3.45 (m, 1H), 3.50 (m, 1H), 3.65 (m, 2H), 3.75 (m, 2H), 4.25 (m, 2H), 4.35 (m, 2H), 4.50 (s, 1H), 6.5-7.0 (m, 2H), 7.1-7.4 (m, 5H).

Workup

  1. extractionthe mixture was extracted with 5 ml ethyl acetate three times
  2. washThe organic layer was washed with saturated sodium bicarbonate, water and brine
  3. dry with materialdried over anhydrous sodium phosphate
  4. concentrationconcentrated under reduced pressure
  5. customThe product was purified by column chromatography

Sources & evidence

ORD record
ord-4f0314a295be43d48a7bce2504ac5e31
Source dataset
uspto-grants-2014_05
Patent number
US08722896B2

Reaction notes

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