1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 67347720, compound

HRID 1397455Notes

Reaction equation

HRID 1397455 reaction equation
C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.C(N(C(C)C)CC)(C)C.[F:31][C:32]([F:53])([F:52])[C:33]1[O:37][N:36]=[C:35]([C:38]2[CH:39]=[C:40]([CH:49]=[CH:50][CH:51]=2)[C:41]([NH:43][CH2:44][CH2:45][C:46]([OH:48])=O)=[O:42])[N:34]=1.O[N:55]=[C:56]([NH2:63])[C:57]1[CH:62]=[CH:61][CH:60]=[CH:59][CH:58]=1>ClCCl.CN(C=O)C.C(OCC)(=O)C.C1(C)C=CC=CC=1>[C:57]1([C:56]2[N:63]=[C:46]([CH2:45][CH2:44][NH:43][C:41](=[O:42])[C:40]3[CH:49]=[CH:50][CH:51]=[C:38]([C:35]4[N:34]=[C:33]([C:32]([F:31])([F:53])[F:52])[O:37][N:36]=4)[CH:39]=3)[O:48][N:55]=2)[CH:62]=[CH:61][CH:60]=[CH:59][CH:58]=1

Participants

10

Reactant 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 69186N'-HydroxybenzenecarboximidamideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 67325165HCID 67325165, compound

Product 1

HCID 67347720HCID 67347720, compoundYield 7%

Reagents, catalysts & solvents 4

HCID 6228DimethylformamideCatalystHCID 1140TolueneSolventHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
90 °C

Procedure

HOBt (47 mg, 0.35 mmol), EDCI (67 mg, 0.35 mmol), and diisopropylethylamine (0.7 mL, 1.0 mmol) were added to a solution of 3-(3-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzamido)propanoic acid (115 mg, 0.35 mmol) and N′-hydroxybenzimidamide (47 mg, 0.35 mmol) in dichloromethane (3.5 mL) with a few drops of DMF. The reaction was stirred 1 h and then toluene was added and the reaction was heated to 90° C. for 1 h. The reaction was diluted with ethyl acetate and the organic layer was washed with saturated sodium bicarbonate and dried over sodium sulfate. The product was purified on reverse phase using water/acetonitrile to give N-(2-(3-phenyl-1,2,4-oxadiazol-5-yl)ethyl)-3-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzamide (10 mg, yield 7%). 1H NMR (CDCl3) δ 8.60 (s, 1H), 8.22 (m, 1H), 8.10 (m, 3H,) 7.60 (m, 1H), 7.55-7.45 (m, 3H), 4.05 (m, 2H), 3.26 (m, 2H). MS (ESI) m/z: Calculated for C20H14F3N5O3: 429.10. found: 430.1 (M+H)+.

Workup

  1. washthe organic layer was washed with saturated sodium bicarbonate
  2. dry with materialdried over sodium sulfate
  3. customThe product was purified on reverse phase

Sources & evidence

ORD record
ord-e67b1c9cd0984f57a8078adc2c7828f8
Source dataset
uspto-grants-2014_12
Patent number
US08901156B2

Reaction notes

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