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1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 57635652, compound

HRID 2110231
Notes
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Reaction equation

HRID 2110231 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:14][CH2:13][CH2:12][N:11]2[C:15]([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)=[N:16][C:17]([C:18]([NH:20][C@@H:21]([C:25]([CH3:28])([CH3:27])[CH3:26])[C:22]([OH:24])=[O:23])=[O:19])=[C:10]2[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].CN(C)CCCN=C=NCC.O.ON1C2C=CC=CC=2N=N1.O[NH:58][C:59](=[NH:61])[CH3:60]>C(Cl)Cl>[NH2:61]/[C:59](=[N:58]\[O:23][C:22](=[O:24])[C@@H:21]([NH:20][C:18]([C:17]1[N:16]=[C:15]([C:29]2[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=2)[N:11]2[CH2:12][CH2:13][CH2:14][N:8]([C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7])[CH2:9][C:10]=12)=[O:19])[C:25]([CH3:27])([CH3:28])[CH3:26])/[CH3:60]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 27960291-Hydroxybenzotriazole hydrateHCID 57635177HCID 57635177, compoundHCID 178465666HCID 178465666, compound

Product 1

HCID 57635652HCID 57635652, compound

Reagents, catalysts & solvents 1

HCID 6344
Dichloromethane
Solvent
3×

Procedure

A 2 mL dichloromethane solution of Compound 515 (320 mg, 0.68 mmol) was added to a dichloromethane solution of N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide (209 mg, 1.09 mmol) and 1-hydroxybenzotriazole hydrate (167 mg, 1.09 mmol). The solution was stirred for 15 minutes at ambient temperature. N-hydroxyacetamidine (76 mg, 1.02 mmol) was added in one portion as a solid, and the mixture was stirred overnight. After diluting with additional DCM, the reaction mixture was washed with saturated aqueous aqueous NaHCO3 solution and brine, dried over anhydrous Na2SO4, and concentrated to a pale yellow foaming solid (Intermediate 49A). LCMS (+ESI) m/z 527.2 [M+H]+.

Workup

  1. stirringthe mixture was stirred overnight
  2. washthe reaction mixture was washed with saturated aqueous aqueous NaHCO3 solution and brine
  3. dry with materialdried over anhydrous Na2SO4
  4. concentrationconcentrated to a pale yellow foaming solid (Intermediate 49A)

Sources & evidence

ORD record
ord-4cb97a3f1d6d4d55a5189f9124790305
Source dataset
uspto-grants-2009_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07517874B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes