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1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 178492636, compound

HRID 420135
Notes
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Reaction equation

HRID 420135 reaction equation
[CH:1]1([N:4]2[C:12]3[C:7](=[C:8]([O:16][CH3:17])[CH:9]=[C:10]([C:13]([OH:15])=O)[CH:11]=3)[CH:6]=[CH:5]2)[CH2:3][CH2:2]1.[O:18]=[C:19]1[C:33]2[C:28](=[CH:29][CH:30]=[C:31]([C:34]3[NH:35][C:36]([C:39]([NH2:41])=[O:40])=[N:37][N:38]=3)[CH:32]=2)[O:27][C:21]2([CH2:26][CH2:25][NH:24][CH2:23][CH2:22]2)[CH2:20]1.C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C>CN(C=O)C.O>[CH:1]1([N:4]2[C:12]3[C:7](=[C:8]([O:16][CH3:17])[CH:9]=[C:10]([C:13]([N:24]4[CH2:23][CH2:22][C:21]5([CH2:20][C:19](=[O:18])[C:33]6[C:28](=[CH:29][CH:30]=[C:31]([C:34]7[NH:35][C:36]([C:39]([NH2:41])=[O:40])=[N:37][N:38]=7)[CH:32]=6)[O:27]5)[CH2:26][CH2:25]4)=[O:15])[CH:11]=3)[CH:6]=[CH:5]2)[CH2:2][CH2:3]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 666494031-cyclopropyl-4-methoxy-1H-indole-6-carboxylic acidHCID 178513836HCID 178513836, compound

Product 1

HCID 178492636HCID 178492636, compound

Reagents, catalysts & solvents 2

HCID 962
Water
Solvent
HCID 6228DimethylformamideSolvent

Procedure

To a solution of 1-cyclopropyl-4-methoxy-1H-indole-6-carboxylic acid (54 mg) and 5-[4-oxo-spiro(chroman-2,4′-piperidin)-6-yl]-4H-1,2,4-triazole-3-carboxamide (102 mg) in DMF (4 mL) were added TEA (77 uL), HOBT (42 mg), and WSC (53 mg) at room temperature and the reaction mixture was stirred at room temperature overnight. The reaction mixture was poured into H2O, extracted with CHCl3, dried over sodium sulfate, filtered, and concentrated in reduced pressure. The residue was purified by column chromatography on silica gel using a mixture of CHCl3/MeOH (1:0-10:1) as eluent to give the title compound as a colorless solid. 1H-NMR (400 MHz, CDCl3) δ: 8.78-8.60 (1H, m), 8.40-8.25 (1H, m), 7.29 (1H, s), 7.15 (1H, d, J=8.0 Hz), 7.09 (1H, d, J=4.0 Hz), 6.57 (1H, s), 6.52 (1H, d, J=4.0 Hz), 4.30-4.17 (1H, m), 3.95 (3H, s), 3.62-3.38 (3H, m), 3.38-3.32 (1H, m), 2.85 (2H, s), 2.28-1.70 (4H, m), 1.06-1.04 (2H, m), 1.00-0.97 (2H, m); MS [M+H]+=541.

Workup

  1. extractionextracted with CHCl3
  2. dry with materialdried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in reduced pressure
  5. customThe residue was purified by column chromatography on silica gel using
  6. additiona mixture of CHCl3/MeOH (1:0-10:1) as eluent

Sources & evidence

ORD record
ord-b4339f12e0aa4de497549e82acd6dc88
Source dataset
uspto-grants-2012_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08093389B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes