1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → HCID 22219496, compound

HRID 1793950Notes

Reaction equation

HRID 1793950 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([CH:8]([CH3:10])[CH3:9])[CH:5]=[CH:4][C:3]=1[CH2:11][CH2:12][NH:13][S:14]([C:17]1[CH:22]=[C:21]([C:23]#[N:24])[CH:20]=[CH:19][C:18]=1[O:25][CH3:26])(=[O:16])=[O:15].[C:27]([N:46]1[C:50]([CH2:51][C:52](O)=[O:53])=[N:49][N:48]=[N:47]1)([C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1)([C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1.O.ON1C2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC>CN(C)C=O.O>[C:23]([C:21]1[CH:20]=[CH:19][C:18]([O:25][CH3:26])=[C:17]([S:14]([NH:13][CH2:12][CH2:11][C:3]2[CH:4]=[CH:5][C:6]([CH:8]([CH3:10])[CH3:9])=[CH:7][C:2]=2[NH:1][C:52](=[O:53])[CH2:51][C:50]2[N:46]([C:27]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)([C:34]3[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=3)[C:40]3[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=3)[N:47]=[N:48][N:49]=2)(=[O:16])=[O:15])[CH:22]=1)#[N:24]

Participants

7

Reactant 4

HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 22219493HCID 22219493, compoundHCID 22219524HCID 22219524, compound

Product 1

HCID 22219496HCID 22219496, compoundYield 94.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of 0.30 g of N-[2-(2-amino-4-isopropylphenyl)ethyl]-5-cyano-2-methoxybezenesulfonamide, 0.298 g of (1-trityl-1H-tetrazol-5-yl)acetic acid and 0.129 g of 1-hydroxybenzotriazole monohydrate in 2.4 mL of N,N-dimethylformamide was added 0.140 g of 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride under ice-cooling, and the mixture was stirred at room temperature for 14 hours. To the reaction mixture was added water, and the mixture was extracted with ethyl acetate. The organic layer was washed with 1 mol/L hydrochloric acid, water, and brine, and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure, and the residue was purified by column chromatography on silica gel (eluent: ethyl acetate-hexane) to give 0.549 g of N-[2-[2-(5-cyano-2-methoxybenzenesulfonylamino)ethyl]-5-isopropylphenyl]-2-(1-trityl-1H-tetrazol-5-yl)acetamide.

Workup

  1. temperaturecooling
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with 1 mol/L hydrochloric acid, water, and brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe solvent was removed under reduced pressure
  6. customthe residue was purified by column chromatography on silica gel (eluent: ethyl acetate-hexane)

Sources & evidence

ORD record
ord-688c926d8cc543f181297bbb9d66ba9e
Source dataset
uspto-grants-2006_04
Patent number
US07022689B2

Reaction notes

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