Dimethylformamide → HCID 57729052, compound

HRID 1988117Notes

Reaction equation

HRID 1988117 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 crystallized in ethyl acetate 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)
  8. customThe oil is crystallized in ethyl acetate

Sources & evidence

ORD record
ord-a5675818c3e341ddad411f854ad666f2
Source dataset
uspto-grants-2009_06
Patent number
US07553965B2

Reaction notes

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