1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → HCID 178450676, compound

HRID 1443388Notes

Reaction equation

HRID 1443388 reaction equation
[C:1]1([C:7]2[N:8]=[C:9]([CH:12]3[CH2:17][CH2:16][CH2:15][CH2:14][NH:13]3)[NH:10][CH:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:18]([O:22][C:23](=[O:53])[C:24]1[CH:29]=[CH:28][C:27]([CH2:30][CH:31]([C:50](O)=[O:51])[NH:32][C:33]([O:35][CH2:36][CH:37]2[C:49]3[CH:48]=[CH:47][CH:46]=[CH:45][C:44]=3[C:43]3[C:38]2=[CH:39][CH:40]=[CH:41][CH:42]=3)=[O:34])=[CH:26][CH:25]=1)([CH3:21])([CH3:20])[CH3:19].Cl.CN(C)CCCN=C=NCC.O.ON1C2C=CC=CC=2N=N1>CN(C)C=O>[C:18]([O:22][C:23](=[O:53])[C:24]1[CH:25]=[CH:26][C:27]([CH2:30][CH:31]([NH:32][C:33]([O:35][CH2:36][CH:37]2[C:38]3[CH:39]=[CH:40][CH:41]=[CH:42][C:43]=3[C:44]3[C:49]2=[CH:48][CH:47]=[CH:46][CH:45]=3)=[O:34])[C:50](=[O:51])[N:13]2[CH2:14][CH2:15][CH2:16][CH2:17][CH:12]2[C:9]2[NH:10][CH:11]=[C:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)[N:8]=2)=[CH:28][CH:29]=1)([CH3:21])([CH3:19])[CH3:20]

Participants

6

Reactant 4

HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 184679482-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-3-(4-(tert-butoxycarbonyl)phenyl)propanoic acidHCID 178420113HCID 178420113, compound

Product 1

HCID 178450676HCID 178450676, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of 182 mg (0.8 mmol) of 2-(4-Phenyl-1H-imidazol-2-yl)-piperidine, 390 mg (0.8 mmol) of 4-[2-carboxy-2-(9H-fluoren-9-ylmethoxycarbonylamino)-ethyl]-benzoic acid tert-butyl ester, 216 mg (1.6 mmol) of 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride, and 192 mg of 1-hydroxybenzotriazole hydrate was added 2.5 mL of dimethylformamide. The mixture was allowed to stir at room temperature overnight. The mixture was then partitioned between ethyl acetate and water. The organic layer was separated, dried over MgSO4 and concentrated to 670 mg of crude product.

Workup

  1. customThe mixture was then partitioned between ethyl acetate and water
  2. customThe organic layer was separated
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated to 670 mg of crude product

Sources & evidence

ORD record
ord-fdc00d6531714b389dcdbf0038d8b9cb
Source dataset
uspto-grants-2010_02
Patent number
US07659402B2

Reaction notes

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