1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 24958965, compound

HRID 2381844Notes

Reaction equation

HRID 2381844 reaction equation
[CH3:1][C:2]1[N:3]=[C:4]([N:10]2[CH:14]=[C:13]([CH2:15][CH2:16][CH2:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[N:12]=[N:11]2)[S:5][C:6]=1[C:7]([OH:9])=O.ON1C2C=CC=CC=2N=N1.CN(C)CCCN=C=NCC.C(N(CC)C(C)C)(C)C.[N:54]1[CH:59]=[CH:58][CH:57]=[C:56]([CH2:60][NH2:61])[CH:55]=1>CN(C)C=O.ClCCl>[CH3:1][C:2]1[N:3]=[C:4]([N:10]2[CH:14]=[C:13]([CH2:15][CH2:16][CH2:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[N:12]=[N:11]2)[S:5][C:6]=1[C:7]([NH:61][CH2:60][C:56]1[CH:55]=[N:54][CH:59]=[CH:58][CH:57]=1)=[O:9]

Participants

8

Reactant 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 310183-PyridinemethanamineHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 59179706HCID 59179706, compound

Product 1

HCID 24958965HCID 24958965, compoundYield 51%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-methyl-2-(4-(3-phenylpropyl)-1H-1,2,3-triazol-1-yl)thiazole-5-carboxylic acid (4.62 g, 14.07) in anhydrous N,N-dimethylformamide (50 mL) was added 1-hydroxybenzotriazole (2.28 g, 16.88 mmol), N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide (3.24 g, 16.88 mmol), N,N-diisopropylethylamine (7.35 mL, 42.20 mmol) and pyridin-3-ylmethanamine (1.72 mL, 16.88 mmol). The reaction mixture was stirred at ambient temperature for 18 hours, diluted with dichloromethane (150 mL) and washed with saturated aqueous sodium bicarbonate (50 mL) and brine (50 mL). The organic layer was dried over anhydrous sodium sulfate, filtered and concentrated in vacuo. The residue was purified by column chromatography to afford the title compound as a white solid in 51% yield (3.00 g): mp 108-110° C. (dichloromethane/hexanes); 1H NMR (300 MHz, DMSO-d6) δ 9.00 (t, J=6.0 Hz, 1H), 8.72 (s, 1H), 8.57 (s, 1H), 8.48 (d, J=6.0 Hz, 1H), 7.77-7.73 (m, 1H), 7.40-7.36 (m, 1H), 7.31-7.18 (m, 5H), 4.47 (d, J=6.0 Hz, 2H), 2.76-2.61 (m, 7H), 2.03-1.95 (m, 2H); 13C NMR (75 MHz, DMSO-d6) δ 160.4, 155.1, 152.6, 148.8, 148.7, 148.2, 141.5, 135.2, 134.5, 128.3, 128.2, 125.7, 123.9, 123.5, 119.7, 40.6, 34.4, 30.1, 24.3, 17.1; MS (ES+) m/z 419.4 (M+1).

Workup

  1. washwashed with saturated aqueous sodium bicarbonate (50 mL) and brine (50 mL)
  2. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-f5979c8a81064e8e899616dd0b858f5e
Source dataset
uspto-grants-2012_09
Patent number
US08258160B2

Reaction notes

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