Carzenide → HCID 62350329, compound

HRID 1520638Notes

Reaction equation

HRID 1520638 reaction equation
[S:1]([C:5]1[CH:13]=[CH:12][C:8]([C:9]([OH:11])=O)=[CH:7][CH:6]=1)(=[O:4])(=[O:3])[NH2:2].[O:14]1[CH2:19][CH2:18][CH:17]([CH2:20][NH2:21])[CH2:16][CH2:15]1.O.ON1C2C=CC=CC=2N=N1.Cl.C(N=C=NCCCN(C)C)C>C(#N)C>[S:1]([C:5]1[CH:6]=[CH:7][C:8]([C:9]([NH:21][CH2:20][CH:17]2[CH2:18][CH2:19][O:14][CH2:15][CH2:16]2)=[O:11])=[CH:12][CH:13]=1)(=[O:3])(=[O:4])[NH2:2]

Participants

6

Reactant 4

HCID 8739CarzenideHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27732104-AminomethyltetrahydropyranHCID 27960291-Hydroxybenzotriazole hydrate

Product 1

HCID 62350329HCID 62350329, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

4-Sulfamoylbenzoic acid (201 mg), (tetrahydro-2H-pyran-4-yl)methanamine (144 mg), 1-hydroxybenzotriazole hydrate (230 mg), and 1-ethyl-3-[3-(dimethylamino)propyl]-carbodiimide hydrochloride (288 mg) were combined in acetonitrile. The mixture was stirred at room temperature overnight. The solids were filtered off and reaction mixture was concentrated. The crude material was purified by flash chromatography eluting with a gradient of 2% methanol/dichloromethane to 10% methanol/dichloromethane.

Workup

  1. filtrationThe solids were filtered off
  2. customreaction mixture
  3. concentrationwas concentrated
  4. customThe crude material was purified by flash chromatography
  5. washeluting with a gradient of 2% methanol/dichloromethane to 10% methanol/dichloromethane

Sources & evidence

ORD record
ord-7813f18695b54339b5ed950fe12a3962
Source dataset
uspto-grants-2015_07
Patent number
US09073855B2

Reaction notes

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