Triethylamine → [(S)-1-(3-Phenylaminopyridin-2-ylcarbamoyl)ethyl]carbamic acid tert-butyl ester

HRID 242972Notes

Reaction equation

HRID 242972 reaction equation
C(N(CC)CC)C.[C:8]1([NH:14][C:15]2[C:16]([NH2:21])=[N:17][CH:18]=[CH:19][CH:20]=2)[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[C:22]([O:26][C:27]([NH:29][C@@H:30]([CH3:34])[C:31](O)=[O:32])=[O:28])([CH3:25])([CH3:24])[CH3:23].C1C=NC2N(O)N=NC=2C=1.Cl.CN(C)CCCN=C=NCC>C(Cl)Cl>[C:22]([O:26][C:27](=[O:28])[NH:29][C@H:30]([C:31](=[O:32])[NH:21][C:16]1[C:15]([NH:14][C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)=[CH:20][CH:19]=[CH:18][N:17]=1)[CH3:34])([CH3:23])([CH3:24])[CH3:25]

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 85082Tert-butoxycarbonylalanineHCID 181649HOAtHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 68018423N3-Phenylpyridine-2,3-diamine

Product 1

HCID 68156995[(S)-1-(3-Phenylaminopyridin-2-ylcarbamoyl)ethyl]carbamic acid tert-butyl esterYield 119.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

Triethylamine (1.5 mL, 11.0 mmol) was added to a mixture of N3-phenylpyridine-2,3-diamine (510 mg, 2.75 mmol), (S)-2-tertbutoxycarbonylaminopropionic acid (0.94 g, 4.96 mmol), HOAt (670 mg, 4.96 mmol) and N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (0.95 g, 4.96 mmol) in anhydrous DCM (30 mL) at 0° C. under a nitrogen atmosphere. The reaction mixture was stirred at 0° C. for 10 min then slowly warmed to RT. Stirring at RT was continued for 18 h. The reaction mixture was partitioned between DCM and a saturated aqueous solution of NaHCO3. The aqueous phase was further extracted with DCM (×3) and the combined organic fractions washed with water, dried (Na2SO4) and concentrated in vacuo to afford the title compound as a light brown foam (1.17 g, quantitative). LCMS (Method C): RT 3.04 min [M+H]+ 357.3.

Workup

  1. temperaturethen slowly warmed to RT
  2. stirringStirring at RT
  3. waitwas continued for 18 h
  4. customThe reaction mixture was partitioned between DCM
  5. extractionThe aqueous phase was further extracted with DCM (×3)
  6. washthe combined organic fractions washed with water
  7. dry with materialdried (Na2SO4)
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-6dcae8cfbd1d486e830b3fd87d3e6bd1
Source dataset
uspto-grants-2014_02
Patent number
US08653089B2

Reaction notes

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