Hydrochloric Acid → HCID 68892678, compound

HRID 1454180Notes

Reaction equation

HRID 1454180 reaction equation
[Cl:1]C1C=CC(C(CCC(O)=O)=O)=CC=1.[CH3:15][N:16]([CH3:30])[C:17]1([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH2:22][CH2:21][CH:20]([NH2:23])[CH2:19][CH2:18]1.CC(N=C=NC(C)C)C.ON1C2C=CC=CC=2N=N1.C(=O)([O-])[O-].[Na+].[Na+].Cl.[Cl:57][C:58]1[CH:63]=[CH:62][C:61]([C:64](=[O:85])[CH2:65][CH2:66][C:67](NC2CCC(N(C)C)(C3C=CC=CC=3)CC2)=[O:68])=[CH:60][CH:59]=1.Cl[Si](C)(C)C>CN(C=O)C.C(OC(=O)C)C.O.C(OC(=O)C)C.C1COCC1>[ClH:1].[Cl:57][C:58]1[CH:59]=[CH:60][C:61]([C:64](=[O:85])[CH2:65][CH2:66][C:67]([NH:23][CH:20]2[CH2:21][CH2:22][C:17]([N:16]([CH3:30])[CH3:15])([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[CH2:18][CH2:19]2)=[O:68])=[CH:62][CH:63]=1

Participants

13

Reactant 8

HCID 313Hydrochloric AcidHCID 6397ChlorotrimethylsilaneHCID 10340Sodium CarbonateHCID 12734DiisopropylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 776043-(4-Chlorobenzoyl)propionic acidHCID 129862564-Dimethylamino-4-phenyl-cyclohexylamineHCID 68891977HCID 68891977, compound

Product 1

HCID 68892678HCID 68892678, compound

Reagents, catalysts & solvents 4

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolventHCID 21939870Tetrahydrofuran ethyl acetateSolvent

Procedure

As described for Example 61, 310 mg 3-(4-chlorobenzoyl) propanoic acid dissolved in 1.6 ml DMF were added to 350 mg of the polar diastereoisomer of N,N-dimethyl-1-phenylcyclohexane-1,4-diamine, 230 [L N,N-diisopropylcarbodiimide and 200 μg 1-hydroxybenzotriazole (HOBt) at 0° C. and while stirring. After three hours at this temperature, the mixture was stirred overnight while heating to room temperature. For working up, one-molar sodium carbonate solution was added (pH>10) and the crude product (1.193 mg) was isolated by extraction with ethylacetate/THF (V:V=1:1), subsequent drying over sodium sulphate and evaporation. The main fraction of 413 mg obtained by column chromatography on silica gel (4.0×18 cm) with methanol/ethylacetate/n-hexane (V:V:V=1:1:1) was dissolved in 41 ml ethylacetate and was converted into the corresponding hydrochloride of the polar diastereoisomer of 4-(4-chloro-phenyl)-N-(4-dimethylamino-4-phenylcyclohexyl)-4-oxobutyramide by adding 18 μl water and 130 μl chlorotrimethylsilane (321 mg white solid).

Workup

  1. stirringthe mixture was stirred overnight
  2. dry with materialsubsequent drying over sodium sulphate and evaporation
  3. customThe main fraction of 413 mg obtained by column chromatography on silica gel (4.0×18 cm) with methanol/ethylacetate/n-hexane (V:V:V=1:1:1)

Sources & evidence

ORD record
ord-d832dedf3f70407b8c606a0c596f6c4f
Source dataset
uspto-grants-2009_01
Patent number
US07476763B2

Reaction notes

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