Triethylamine → HCID 11706086, compound

HRID 852342Notes

Reaction equation

HRID 852342 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH2:9][C:10]([NH:12][CH:13]([CH2:17][CH2:18][CH3:19])[C:14]([OH:16])=O)=[O:11])[CH:5]=[C:6]([F:8])[CH:7]=1.[C:20]1([CH:26]([CH3:35])[CH2:27][S:28][C:29]2[S:33][C:32]([NH2:34])=[N:31][N:30]=2)[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.CCN=C=NCCCN(C)C.Cl.C(N(CC)CC)C>C(Cl)Cl>[C:20]1([CH:26]([CH3:35])[CH2:27][S:28][C:29]2[S:33][C:32]([NH:34][C:14](=[O:16])[CH:13]([NH:12][C:10](=[O:11])[CH2:9][C:4]3[CH:5]=[C:6]([F:8])[CH:7]=[C:2]([F:1])[CH:3]=3)[CH2:17][CH2:18][CH3:19])=[N:31][N:30]=2)[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 219429862-[2-(3,5-Difluoro-phenyl)-acetylamino]-pentanoic acidHCID 68834228HCID 68834228, compound

Product 1

HCID 11706086HCID 11706086, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 2-[2-(3,5-difluoro-phenyl)-acetylamino]-pentanoic acid (25.4 mg, 0.2 mmol), 5-(2-phenyl-propylsulfanyl)-[1,3,4]thiadiazol-2-ylamine (50 mg, 0.2 mmol), HBOT (29 mg, 0.21 mmol), EDC HCl (46 mg, 0.24 mmol.) and triethylamine (0.12 ml) in methylene chloride was stirred at room temperature until product formation or disappearance of starting material. The mixture was quenched with water and extracted with methylene chloride. The organic layer was separated, washed with dilute HCl, brine, dried over sodium sulfate and the solvent was removed at reduced pressure to provide the title compound as a cude oil. The oil was purified by Shimadzu HPLC to provide the title compound as a light yellow solid (26 mg), LC-MS M+1=505.0

Workup

  1. customThe mixture was quenched with water
  2. extractionextracted with methylene chloride
  3. customThe organic layer was separated
  4. washwashed with dilute HCl, brine
  5. dry with materialdried over sodium sulfate
  6. customthe solvent was removed at reduced pressure

Sources & evidence

ORD record
ord-7b5ef962107245809ef22689f56927e3
Source dataset
uspto-grants-2007_08
Patent number
US07253195B2

Reaction notes

Loading…