1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 22710831, compound

HRID 352980Notes

Reaction equation

HRID 352980 reaction equation
[C:1]([O:5][C:6]([CH:8]1[NH:13][CH2:12][C:11]2S[C:15]([C:17]([O-:19])=O)=[N:16][C:10]=2[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[Li+].Cl.[Cl:22][C:23]1[CH:24]=[CH:25][C:26]2[CH:30]=[C:29]([S:31]([N:34]3[CH2:39][CH2:38][NH:37][CH2:36][CH2:35]3)(=[O:33])=[O:32])[S:28][C:27]=2[CH:40]=1.O.[OH:42]N1C2C=CC=CC=2N=N1.CN(C)CCCN=C=NCC>CN(C)C=O.O.C(OCC)(=O)C>[C:1]([O:5][C:6]([CH:8]1[NH:13][CH2:12][C:11]2[O:42][C:15]([C:17]([N:37]3[CH2:38][CH2:39][N:34]([S:31]([C:29]4[S:28][C:27]5[CH:40]=[C:23]([Cl:22])[CH:24]=[CH:25][C:26]=5[CH:30]=4)(=[O:33])=[O:32])[CH2:35][CH2:36]3)=[O:19])=[N:16][C:10]=2[CH2:9]1)=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

8

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 27960291-Hydroxybenzotriazole hydrateHCID 22710719HCID 22710719, compoundHCID 23674321HCID 23674321, compound

Product 1

HCID 22710831HCID 22710831, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of lithium 6-(tert-butoxycarbonyl)-4,5,6,7-tetrahydrothiazolo[5,4-c]pyridine-2-carboxylate (70.0 mg) in N,N-dimethylformamide (4.0 ml) were added 1-[(6-chlorobenzo[b]thien-2-yl)sulfonyl]piperazine hydrochloride (90.0 mg), 1-hydroxybenzotriazole monohydrate (7.0 mg) and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide (64.0 mg) at room temperature. After stirring for 2 days, ethyl acetate (30 ml) and water (500 ml) were added to the reaction mixture to separate it into layers. The water layer was extracted with ethyl acetate (30 ml). The organic layers were combined, washed with a saturated aqueous solution of sodium bicarbonate (100 ml), dried over anhydrous sodium sulfate and distilled under reduced pressure to remove the solvent. The residue was purified by preparative thin-layer chromatography (hexane:ethyl acetate=1:1) using silica gel, whereby the title compound (37.9 mg) was obtained as a colorless transparent glassy substance.

Workup

  1. customto separate it into layers
  2. extractionThe water layer was extracted with ethyl acetate (30 ml)
  3. washwashed with a saturated aqueous solution of sodium bicarbonate (100 ml)
  4. dry with materialdried over anhydrous sodium sulfate
  5. distillationdistilled under reduced pressure
  6. customto remove the solvent
  7. customThe residue was purified by preparative thin-layer chromatography (hexane:ethyl acetate=1:1)
  8. customwas obtained as a colorless transparent glassy substance

Sources & evidence

ORD record
ord-94e8b98d1e1e4bd68cf0f32ae1ed3451
Source dataset
uspto-grants-2004_06
Patent number
US06747023B1

Reaction notes

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