Diethylamine → HCID 71247102, compound

HRID 1519104Notes

Reaction equation

HRID 1519104 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8]([NH:11][C:12]([CH3:30])([CH3:29])[C:13]([NH:15][CH:16]1[CH:23]2[CH2:24][C:19]3([C:26](O)=[O:27])[CH2:20][CH:21]([CH2:25][CH:17]1[CH2:18]3)[CH2:22]2)=[O:14])(=[O:10])=[O:9].Cl.C(N=C=NCCCN(C)C)C.ON1C2C=CC=CC=2N=N1.[CH2:53]([NH:55][CH2:56][CH3:57])[CH3:54]>O.C(Cl)Cl>[CH2:53]([N:55]([CH2:56][CH3:57])[C:26]([C:19]12[CH2:18][CH:17]3[CH2:25][CH:21]([CH2:22][CH:23]([CH:16]3[NH:15][C:13](=[O:14])[C:12]([NH:11][S:8]([C:3]3[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=3[Cl:1])(=[O:9])=[O:10])([CH3:29])[CH3:30])[CH2:24]1)[CH2:20]2)=[O:27])[CH3:54]

Participants

7

Reactant 4

HCID 8021DiethylamineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 71246455HCID 71246455, compound

Product 1

HCID 71247102HCID 71247102, compoundYield 41%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

In a 25-mL flask, 4-[2-(2-chloro-benzenesulfonylamino)-2-methyl-propionylamino]-adamantane-1-carboxylic acid (100 mg, 0.22 mmol), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (85 mg, 0.44 mmol), 1-hydroxybenzotriazol (60 mg, 0.44 mmol), and methylenechloride (10 mL) were charged, and stirred for 15 minutes at room temperature. Then, diethylamine (48 mg, 0.66 mmol) was added thereto, followed by stirring for 12 hours at room temperature. Purified water (5 mL) was added thereto, followed by stirring for 5 minutes. Then, the organic layer was separated, and added with magnesium sulfate (50 mg) so as to remove remaining moisture. The filtrate was concentrated and obtained as a residue. The mixture was purified with column chromatography (MC/MeOH=20:1) to obtain 4-[2-(2-chloro-benzenesulfonylamino)-2-methyl-propionylamino]-adamantane-1-carboxylic acid diethylamide (46 mg, 41.0%).

Workup

  1. stirringby stirring for 12 hours at room temperature
  2. stirringby stirring for 5 minutes
  3. customThen, the organic layer was separated
  4. additionadded with magnesium sulfate (50 mg) so as
  5. customto remove
  6. concentrationThe filtrate was concentrated
  7. customobtained as a residue
  8. customThe mixture was purified with column chromatography (MC/MeOH=20:1)

Sources & evidence

ORD record
ord-a3c7ca3808644b508e6410677c808a9a
Source dataset
uspto-grants-2015_07
Patent number
US09073830B2

Reaction notes

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