1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 74982825, compound

HRID 1910477Notes

Reaction equation

HRID 1910477 reaction equation
[NH2:1][C:2]1[N:7]=[N:6][C:5]([CH2:8][CH2:9][CH2:10][CH2:11][C:12]2[S:16][C:15]([NH:17][C:18](=[O:26])[CH2:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)=[N:14][N:13]=2)=[CH:4][CH:3]=1.[CH3:27][C:28]1[O:32][C:31]([CH2:33][C:34]2[CH:35]=[C:36]([CH2:40][C:41](O)=[O:42])[CH:37]=[CH:38][CH:39]=2)=[N:30][N:29]=1.C(N=C=NCCCN(C)C)C.ON1C2C=CC=CC=2N=N1>CN(C=O)C.O>[CH3:27][C:28]1[O:32][C:31]([CH2:33][C:34]2[CH:35]=[C:36]([CH2:40][C:41]([NH:1][C:2]3[N:7]=[N:6][C:5]([CH2:8][CH2:9][CH2:10][CH2:11][C:12]4[S:16][C:15]([NH:17][C:18](=[O:26])[CH2:19][C:20]5[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=5)=[N:14][N:13]=4)=[CH:4][CH:3]=3)=[O:42])[CH:37]=[CH:38][CH:39]=2)=[N:30][N:29]=1

Participants

7

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 74982604HCID 74982604, compoundHCID 86687872HCID 86687872, compound

Product 1

HCID 74982825HCID 74982825, compoundYield 7.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of N-(5-(4-(6-aminopyridazin-3-yl)butyl)-1,3,4-thiadiazol-2-yl)-2-phenylacetamide 348 (0.035 g, 0.094 mmol), 2-(3-((5-methyl-1,3,4-oxadiazol-2-yl)methyl)phenyl)acetic acid 1107 (0.023 g, 0.094 mmol), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (0.045 g, 0.235 mmol), 1-hydroxybenzotriazole (0.032 g, 0.235 mmol) in DMF (1.75 mL) was stirred for 16 hours and diluted with water (20 mL). The mixture was extracted with EtOAc (3×20 mL) the organic layers combined, washed with water (3×20 mL), brine (2×20 mL) and dried over Na2SO4. The Na2SO4 was removed by filtration and the volatiles removed under reduced pressure. The crude material was purified by reverse phase chromatography giving 0.004 g of 2-(3-((5-methyl-1,3,4-oxadiazol-2-yl)methyl)phenyl)-N-(6-(4-(5-(2-phenylacetamido)-1,3,4-thiadiazol-2-yl)butyl)pyridazin-3-yl)acetamide 652. 1H NMR 300 MHz DMSO-d6: δ 12.62 (s, 1H), 11.24 (s, 1H), 8.16 (d, 1H, J=12.2 Hz), 7.54 (d, 1H, J=12.2 Hz), 7.3-7.1 (m, 9H), 4.20 (s, 2H), 3.78 (s, 2H), 3.74 (s, 2H), 2.99 (m, 2H), 2.87 (m, 2H), 2.41 (s, 3H), 1.72 (m, 4H).

Workup

  1. extractionThe mixture was extracted with EtOAc (3×20 mL) the organic layers
  2. washwashed with water (3×20 mL), brine (2×20 mL)
  3. dry with materialdried over Na2SO4
  4. customThe Na2SO4 was removed by filtration
  5. customthe volatiles removed under reduced pressure
  6. customThe crude material was purified by reverse phase chromatography

Sources & evidence

ORD record
ord-f65f11f5ea984c08a2b62047f09c025d
Source dataset
uspto-grants-2013_12
Patent number
US08604016B2

Reaction notes

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