Triethylamine → HCID 9811366, compound

HRID 1978491Notes

Reaction equation

HRID 1978491 reaction equation
[N:1]1[CH:2]=[C:3]2[N:12]3[C:7](=[CH:8][CH:9]=[CH:10][C:11]=13)[S:6][C:5]([C:13]([OH:15])=O)=[CH:4]2.ON1C(=O)CCC1=O.Cl.C(N=C=NCCCN(C)C)C.C(N(CC)CC)C.[NH2:43][CH:44]1[CH2:49][CH2:48][N:47]([CH2:50][CH2:51][CH2:52][C:53]2[CH:58]=[CH:57][CH:56]=[CH:55][CH:54]=2)[CH2:46][CH2:45]1>C(#N)C.C(Cl)(Cl)Cl>[C:53]1([CH2:52][CH2:51][CH2:50][N:47]2[CH2:48][CH2:49][CH:44]([NH:43][C:13]([C:5]3[S:6][C:7]4[N:12]5[C:3](=[CH:2][N:1]=[C:11]5[CH:10]=[CH:9][CH:8]=4)[CH:4]=3)=[O:15])[CH2:45][CH2:46]2)[CH:54]=[CH:55][CH:56]=[CH:57][CH:58]=1

Participants

8

Reactant 5

HCID 8471TriethylamineHCID 80170N-HydroxysuccinimideHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 10878635HCID 10878635, compoundHCID 10943925HCID 10943925, compound

Product 1

HCID 9811366HCID 9811366, compound

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6342AcetonitrileSolvent2×

Procedure

While 39.11 g (0.1792 mol) of 5-thia-1,8b-diazaacenaphthylene-4-carboxylic acid and 21.7 g (0.188 mol) of N-hydroxysuccinimide were stirred together in 500 ml of acetonitrile, 36.1 g (0.188 mol) of 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride was added, and the mixture was stirred at room temperature overnight. To this reaction mixture was added 30.0 ml (0.215 mol) of triethylamine and, then, a solution of 39.1 g (0.179 mol) of 4-amino-1-(3-phenylpropan-1-yl)piperidine in acetonitrile (100 ml)-chloroform (50 ml) was added. The mixture was stirred at room temperature for 1 hour and the resulting orange-colored precipitate was recovered by filtration and rinsed with acetonitrile (yield 55.75 g). This crude product was purified by silica gel column chromatography (ethyl acetate to ethyl acetate/methanol : 4/1˜1/1) and recrystallization from chloroform-ethanol to provide the title compound.

Workup

  1. stirringThe mixture was stirred at room temperature for 1 hour
  2. filtrationthe resulting orange-colored precipitate was recovered by filtration
  3. washrinsed with acetonitrile (yield 55.75 g)
  4. customThis crude product was purified by silica gel column chromatography (ethyl acetate to ethyl acetate/methanol : 4/1˜1/1) and recrystallization from chloroform-ethanol

Sources & evidence

ORD record
ord-2e20ff30265748b2b59849a2bf290cbc
Source dataset
uspto-grants-2001_05
Patent number
US06235731B1

Reaction notes

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