Triethylamine → HCID 89544959, compound

HRID 2283441Notes

Reaction equation

HRID 2283441 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]([NH2:11])[CH2:9][CH3:10])=[C:4]([F:12])[C:3]=1[C:13]([C:15]1[CH:16]=[N:17][CH:18]=[CH:19][CH:20]=1)=[O:14].[N:21]1([C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])[CH2:25][CH:24]=[C:23]([C:26](OCC)=[O:27])[CH2:22]1.C(N=C=NCCCN(C)C)C.ON1C2N=CC=CC=2N=N1.C(N(CC)CC)C>C(Cl)Cl>[C:34]([O:33][C:31]([N:21]1[CH2:25][CH:24]=[C:23]([C:26](=[O:27])[NH:11][C@H:8]([C:5]2[CH:6]=[CH:7][C:2]([Cl:1])=[C:3]([C:13]([C:15]3[CH:16]=[N:17][CH:18]=[CH:19][CH:20]=3)=[O:14])[C:4]=2[F:12])[CH2:9][CH3:10])[CH2:22]1)=[O:32])([CH3:37])([CH3:36])[CH3:35]

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 181649HOAtHCID 538881261-tert-Butyl 3-ethyl 2,5-dihydro-1H-pyrrole-1,3-dicarboxylateHCID 89544703HCID 89544703, compound

Product 1

HCID 89544959HCID 89544959, compoundYield 85.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To (1S)-1-{4-chloro-2-fluoro-3-[(pyridin-3-yl)carbonyl]phenyl}propan-1-amine (0.1 g, 0.3 mmol) (Example 26) in DCM was added 1-tert-butyl 3-ethyl 1H-pyrrole-1,3(2H,5H)-dicarboxylate (0.065, 0.3 mmol), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (0.07 mg, 0.36 mmol), 1-hydroxy-7-azabenzotriazole (0.049 g, 0.36 mmol) and triethylamine (0.085 ml, 0.6 mmol), then stirred at ambient for 18 hours. The reaction was diluted with DCM washed with 5% citric acid, sat. sodium bicarbonate then brine. The organic extract was dried (Na2SO4), filtered and concentrated to give 3-{(S)-1-[4-Chloro-2-fluoro-3-(pyridine-3-carbonyl)-phenyl]-propylcarbamoyl}-2,5-dihydro-pyrrole-1-carboxylic acid tert-butyl ester (0.125 g). MS: [M+H]+ 488.

Workup

  1. washwashed with 5% citric acid, sat. sodium bicarbonate
  2. extractionThe organic extract
  3. dry with materialwas dried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-c6c392a8af0d49e4b1ff01150bca9e39
Source dataset
uspto-grants-2015_09
Patent number
US09145354B2

Reaction notes

Loading…