Triethylamine → HCID 68157391, compound

HRID 242936Notes

Reaction equation

HRID 242936 reaction equation
C(N(CC)CC)C.[C:8]1([CH3:22])[CH:13]=[CH:12][CH:11]=[C:10]([NH:14][C:15]2[C:20]([NH2:21])=[CH:19][CH:18]=[CH:17][N:16]=2)[CH:9]=1.[C:23]([O:27][C:28]([NH:30][C@@H:31]([CH3:35])[C:32](O)=[O:33])=[O:29])([CH3:26])([CH3:25])[CH3:24].C1C=NC2N(O)N=NC=2C=1.Cl.CN(C)CCCN=C=NCC>C(Cl)Cl>[C:23]([O:27][C:28](=[O:29])[NH:30][C@H:31]([C:32](=[O:33])[NH:21][C:20]1[C:15]([NH:14][C:10]2[CH:9]=[C:8]([CH3:22])[CH:13]=[CH:12][CH:11]=2)=[N:16][CH:17]=[CH:18][CH:19]=1)[CH3:35])([CH3:24])([CH3:25])[CH3:26]

Participants

7

Reactant 5

HCID 8471Triethylamine2×HCID 85082Tert-butoxycarbonylalanine2×HCID 181649HOAt2×HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride2×HCID 22724430HCID 22724430, compound

Product 1

HCID 68157391HCID 68157391, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

Triethylamine (1.7 mL, 12.0 mmol) was added to a mixture of N2-m-tolylpyridine-2,3-diamine (600 mg, 3.01 mmol), (S)-2-tertbutoxycarbonylaminopropionic acid (1.03 g, 5.42 mmol), HOAt (740 mg, 5.42 mmol) and N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (1.04 g, 5.42 mmol) in anhydrous DCM (25 mL) at 0° C. under a nitrogen atmosphere. The reaction mixture was stirred at 0° C. for 15 min then slowly warmed to RT. Stirring at RT was continued for 16 h. After re-cooling the mixture to 0° C., additional amounts of (S)-2-tertbutoxycarbonylaminopropionic acid (220 mg, 1.20 mmol), HOAt (160 mg, 1.20 mmol), N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (230 mg, 1.20 mmol) and triethylamine (0.41 mL, 3.01 mmol) were added. The reaction mixture was stirred at 0° C. for 15 min then slowly warmed to RT. Stirring at RT was continued for 72 h. The reaction mixture was partitioned between DCM and a saturated solution of NaHCO3. The aqueous phase was extracted with DCM (×3) and the combined organic fractions were washed with water, dried (Na2SO4) and concentrated in vacuo to afford the title compound as an off-white foam. The crude material was used without further purification in the following step. Yield assumed to be quantitative. LCMS (Method C): RT 2.70 min [M+H]+ 371.3.

Workup

  1. temperaturethen slowly warmed to RT
  2. stirringStirring at RT
  3. waitwas continued for 16 h
  4. temperatureAfter re-cooling the mixture to 0° C.
  5. stirringThe reaction mixture was stirred at 0° C. for 15 min
  6. temperaturethen slowly warmed to RT
  7. stirringStirring at RT
  8. waitwas continued for 72 h
  9. customThe reaction mixture was partitioned between DCM
  10. extractionThe aqueous phase was extracted with DCM (×3)
  11. washthe combined organic fractions were washed with water
  12. dry with materialdried (Na2SO4)
  13. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-395e9f262c7a4e37a2fd8e30468b4ff2
Source dataset
uspto-grants-2014_02
Patent number
US08653089B2

Reaction notes

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