Dimethylformamide → HCID 57729052, compound

HRID 1444609Notes

Reaction equation

HRID 1444609 reaction equation
Cl.CN(C)CCCN=C=NCC.C([N:15]([CH2:18][CH3:19])[CH2:16][CH3:17])C.[OH:20]N1C2C=CC=CC=2N=N1.Cl.[CH3:31][O:32][C:33]1[CH:34]=[C:35]2[C:46]3[CH:39]([CH2:40][CH2:41][C:42]=3[C:43]=1[O:44][CH3:45])[NH:38][CH2:37][CH2:36]2.CN(C)[CH:49]=[O:50]>C(Cl)Cl.O>[CH3:31][O:32][C:33]1[CH:34]=[C:35]2[C:46]3[CH:39]([CH2:40][CH2:41][C:42]=3[C:43]=1[O:44][CH3:45])[N:38]([C:49](=[O:50])[CH2:19][CH2:18][NH:15][C:16](=[O:20])[CH3:17])[CH2:37][CH2:36]2

Participants

8

Reactant 5

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 67358446HCID 67358446, compound

Product 1

HCID 57729052HCID 57729052, compoundYield 66%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

A suspension of N-(3-Dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (1.14 g, 5.93 mmol) and triethylamine (4 ml) in N,N-Dimethylformamide (30 ml) is stirred at room temperature. Then, 1-Hydroxybenzotriazole (0.698 g, 4.56 mmol), 7,8-Dimethoxy-1,2,2a,3,4,5-hexahydro-3-aza-acenaphthylene hydrochloride (1.0 g, 4.56 mmol) and N-acetil-3-aminopropanoic acid (0.657 g; 5.0 mmol) were added and the crude is stirred at room temperature for 15 h. Then, water (60 ml) and CH2Cl2 (60 ml) are added to the crude. Organic layer is separated and the aqueous one is extracted with CH2Cl2 (2×60 ml). All the organic layers were collected and washed with 0.1 N HCl (3×60 ml), with NaHCO3 (3×60 ml) sat and with water (3×40 ml). After drying with Na2SO4, filtration and vacuum concentration, a beige oil is obtained (1.32 g, 87% yield). The oil is cristallized in ethyl acete to give a beige solid (1.0 g, 66% yield).

Workup

  1. stirringthe crude is stirred at room temperature for 15 h
  2. customOrganic layer is separated
  3. extractionthe aqueous one is extracted with CH2Cl2 (2×60 ml)
  4. customAll the organic layers were collected
  5. washwashed with 0.1 N HCl (3×60 ml), with NaHCO3 (3×60 ml)
  6. dry with materialAfter drying with Na2SO4, filtration and vacuum concentration
  7. customa beige oil is obtained (1.32 g, 87% yield)

Sources & evidence

ORD record
ord-e0ef760a60e442ff89043b2352a7719a
Source dataset
uspto-grants-2010_02
Patent number
US07662862B2

Reaction notes

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