Triethylamine → HCID 11706086, compound

HRID 2217774Notes

Reaction equation

HRID 2217774 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-90e95e4c49a7493ca69cc9fb895e7380
Source dataset
uspto-grants-2008_08
Patent number
US07408068B2

Reaction notes

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