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1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → HCID 66726297, compound

HRID 1024503
Notes
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Reaction equation

HRID 1024503 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.[C:19]([O:23][C:24]([N:26]1[CH2:31][CH2:30][S:29][CH:28]([C:32](O)=[O:33])[CH2:27]1)=[O:25])([CH3:22])([CH3:21])[CH3:20].Cl.C(N=C=NCCCN(C)C)C.CC1C=CN=C(N)C=1C>ClCCl.O>[C:19]([O:23][C:24]([N:26]1[CH2:31][CH2:30][S:29][CH:28]([C:32]([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]([CH3:18])[CH3:17])=[O:33])[CH2:27]1)=[O:25])([CH3:22])([CH3:21])[CH3:20]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27606194-(Tert-butoxycarbonyl)thiomorpholine-2-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 66726297HCID 66726297, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

The mixture of N-(9-chloro-3,4-dihydro-2H-1,5-benzodioxepin-7-ylmethyl)-2-methylpropan-1-amine (150 mg), thiomorpholine-2,4-dicarboxylic acid 4-tert-butyl ester (137 mg), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (138 mg), and dimethyl aminopyridine (92 mg) in dichloromethane (15 ml) was stirred at room temperature overnight. After the addition of water (10 ml), the mixture was extracted with 10 ml ethyl acetate three times. The organic layer was washed with saturated sodium bicarbonate, water and brine, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The crude was purified by column chromatography on silica (20-33% ethyl acetate in hexane) to give the desired product as a resin: MS (m+1)=499.4.

Workup

  1. extractionthe mixture was extracted with 10 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 sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe crude was purified by column chromatography on silica (20-33% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-a0615283dd4243e3a2b91e33cbddf470
Source dataset
uspto-grants-2014_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08722896B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes