Triethylamine → HCID 86711373, compound

HRID 532925Notes

Reaction equation

HRID 532925 reaction equation
[NH2:1][CH2:2][C:3]([N:5]1[CH:14]([CH2:15][C:16](O)=[O:17])[C:13]2[N:12]=[CH:11][CH:10]=[C:9]([Cl:19])[C:8]=2[CH2:7][CH2:6]1)=[O:4].C(N(CC)CC)C.C([O-])(O)=O.[Na+]>C(Cl)Cl.C(P1(=O)OP(CCC)(=O)OP(CCC)(=O)O1)CC.CCOC(C)=O>[Cl:19][C:9]1[C:8]2[CH2:7][CH2:6][N:5]3[C:3](=[O:4])[CH2:2][NH:1][C:16](=[O:17])[CH2:15][CH:14]3[C:13]=2[N:12]=[CH:11][CH:10]=1

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 516892Sodium BicarbonateHCID 86711372HCID 86711372, compound

Product 1

HCID 86711373HCID 86711373, compoundYield 17.6%

Reagents, catalysts & solvents 3

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolventHCID 111923Propylphosphonic anhydrideSolvent

Procedure

94-9. To a stirred solution of 2-(7-(2-aminoacetyl)-4-chloro-5,6,7,8-tetrahydro-1,7-naphthyridin-8-yl)acetic acid (HCl-salt) (450 mg, 1.41 mmol) and triethylamine (1.17 mL, 8.43 mmol) in DCM (20 mL), T3P (1.25 mL, 2.11 mmol, 50% m/m in AcOEt) was added slowly and the suspension was stirred at RT for 1 h. Saturated aqueous NaHCO3 solution was added and the mixture was extracted with DCM (2×). The combined organic layers were dried with sodium sulfate, filtered and the solvent was removed under reduced pressure. The crude product was purified by flash-column chromatography over silicagel (Biotage Isolera One, eluent: gradient from 2% MeOH in AcOEt to 15% MeOH in AcOEt in 18 min) to yield the title compound as a beige solid (66 mg). UPLC-MS: MS 266.1 (M+H+); UPLC rt 0.57 min.

Workup

  1. extractionthe mixture was extracted with DCM (2×)
  2. dry with materialThe combined organic layers were dried with sodium sulfate
  3. filtrationfiltered
  4. customthe solvent was removed under reduced pressure
  5. customThe crude product was purified by flash-column chromatography over silicagel (Biotage Isolera One, eluent: gradient from 2% MeOH in AcOEt to 15% MeOH in AcOEt in 18 min)

Sources & evidence

ORD record
ord-d5fdc61575634e6b8397281b2f8fa95e
Source dataset
uspto-grants-2014_10
Patent number
US08853203B2

Reaction notes

Loading…