1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 46830534, compound

HRID 705101Notes

Reaction equation

HRID 705101 reaction equation
N=C=N.[CH:4]([C:7]1[N:8]=[N:9][S:10][C:11]=1[C:12]1[CH:13]=[C:14]([CH:18]=[C:19]([C:21]2[CH:26]=[CH:25][C:24]([CH3:27])=[CH:23][N:22]=2)[CH:20]=1)[C:15](O)=[O:16])([CH3:6])[CH3:5].[CH3:28][C:29]1[N:30]=[CH:31][C:32]([CH2:35][NH2:36])=[N:33][CH:34]=1.CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1>C(Cl)Cl.CCN(CC)CC>[CH:4]([C:7]1[N:8]=[N:9][S:10][C:11]=1[C:12]1[CH:13]=[C:14]([CH:18]=[C:19]([C:21]2[CH:26]=[CH:25][C:24]([CH3:27])=[CH:23][N:22]=2)[CH:20]=1)[C:15]([NH:36][CH2:35][C:32]1[CH:31]=[N:30][C:29]([CH3:28])=[CH:34][N:33]=1)=[O:16])([CH3:6])[CH3:5]

Participants

8

Reactant 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 160435CarbodiimideHCID 27564962-(Aminomethyl)-5-methylpyrazineHCID 59370290HCID 59370290, compound

Product 1

HCID 46830534HCID 46830534, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8471TriethylamineSolvent

Procedure

3-(4-Isopropyl-[1,2,3]thiadiazol-5-yl)-N-(5-methyl-pyrazin-2-ylmethyl)-5-(5-methyl-pyridin-2-yl)-benzamide was prepared using the carbodiimide-based amide synthesis procedure of example 7 in published patent application US2008004442. Briefly, 3-(4-isopropyl-[1,2,3]thiadiazol-5-yl)-5-(5-methyl-pyridin-2-yl)-benzoic acid, C-(5-methyl-pyrazin-2-yl)-methylamine, EDCI, HOBt and Et3N were added to methylene chloride, and the mixture was stirred at room temperature for 16 hours, then was partitioned between water and methylene chloride. The combined organic layers were dried (MgSO4), filtered and concentrated under reduced pressure. The resulting residue was purified via flash chromatography to give3-(4-isopropyl-[1,2,3]thiadiazol-5-yl)-N-(5-methyl-pyrazin-2-ylmethyl)-5-(5-methyl-pyridin-2-yl)-benzamide, MS (M+H)=445.

Workup

  1. customwas partitioned between water and methylene chloride
  2. dry with materialThe combined organic layers were dried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe resulting residue was purified via flash chromatography to give3-(4-isopropyl-[1,2,3]thiadiazol-5-yl)-N-(5-methyl-pyrazin-2-ylmethyl)-5-(5-methyl-pyridin-2-yl)-benzamide, MS (M+H)=445

Sources & evidence

ORD record
ord-df0dcaf65bdc4ecc88330166ac4652b9
Source dataset
uspto-grants-2015_11
Patent number
US09173861B2

Reaction notes

Loading…