1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 11682270, compound

HRID 1096505Notes

Reaction equation

HRID 1096505 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][C:6]([C:10]([OH:12])=O)=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.[C:34]1([N:40]2[C:44]3([CH2:49][CH2:48][NH:47][CH2:46][CH2:45]3)[C:43](=[O:50])[NH:42][CH2:41]2)[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1>CN(C=O)C.O>[NH:1]1[C:9]2[C:4](=[CH:5][C:6]([C:10]([N:47]3[CH2:46][CH2:45][C:44]4([N:40]([C:34]5[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=5)[CH2:41][NH:42][C:43]4=[O:50])[CH2:49][CH2:48]3)=[O:12])=[CH:7][CH:8]=2)[CH:3]=[CH:2]1

Participants

7

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 705561-Phenyl-1,3,8-triazaspiro(4.5)decan-4-oneHCID 742801H-Indole-5-Carboxylic AcidHCID 757711-Hydroxybenzotriazole

Product 1

HCID 11682270HCID 11682270, compoundYield 67.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a mixture of indole-5-carboxylic acid (300 mg, 1.86 mmol) and HOBT (278 mg, 2.05 mmol) in dry DMF (10 mL) was added EDAC (464 mg, 2.42 mmol). The resulting mixture was stirred for 10 min followed by addition of a mixture of TEA (0.78 ml, 5.58 mmol) and 1-phenyl-1,3,8-triaza-spiro[4.5]decan-4-one (473 mg, 2.04 mmol). The reaction mixture was stirred for an additional 16 hrs. To the reaction mixture was added water (25 ml) and the resulting precipitate was filtered and washed with water. The resulting solid was recrystalised from a mixture of EtOH-water (4:1, 10 mL) the precipitate was filtered off, washed with water and dried in vacuo at 40° C. affording 472 mg (67%) of the title compound as a solid.

Workup

  1. stirringThe reaction mixture was stirred for an additional 16 hrs
  2. filtrationthe resulting precipitate was filtered
  3. washwashed with water
  4. customThe resulting solid was recrystalised from a mixture of EtOH-water (4:1, 10 mL) the precipitate
  5. filtrationwas filtered off
  6. washwashed with water
  7. customdried in vacuo at 40° C.

Sources & evidence

ORD record
ord-06d373c53afb4099b708c8b45caec14b
Source dataset
uspto-grants-2012_03
Patent number
US08138342B2

Reaction notes

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