Triethylamine → HCID 60205435, compound

HRID 408273Notes

Reaction equation

HRID 408273 reaction equation
[Br:1][C:2]1[C:3]([F:12])=[C:4]2[C:10]([NH2:11])=[CH:9][NH:8][C:5]2=[N:6][CH:7]=1.[CH3:13][O:14][CH2:15][CH2:16][C:17](O)=[O:18].C(N(CC)CC)C.C1N(P(Cl)(N2C(=O)OCC2)=O)C(=O)OC1.O[Li].O>C(Cl)Cl.O>[Br:1][C:2]1[C:3]([F:12])=[C:4]2[C:10]([NH:11][C:17](=[O:18])[CH2:16][CH2:15][O:14][CH3:13])=[CH:9][NH:8][C:5]2=[N:6][CH:7]=1

Participants

8

Reactant 5

HCID 8471TriethylamineHCID 1344423-Methoxypropionic acidHCID 152842Bis(2-oxo-3-oxazolidinyl)phosphinic chlorideHCID 168937Lithium hydroxide, monohydrateHCID 602052765-bromo-4-fluoro-1H-pyrrolo[2,3-b]pyridin-3-amine

Product 1

HCID 60205435HCID 60205435, compoundYield 42%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of 5-bromo-4-fluoro-1H-pyrrolo[2,3-b]pyridin-3-amine (200 mg, 0.869 mmol, Example 1, Step H), 3-methoxypropanoic acid (204.2 μL, 2.174 mmol) and triethylamine (605.9 μL, 4.347 mmol) in CH2Cl2 (10 mL) at room temperature was treated with BOP-Cl (202.7 mg, 2.174 mmol). The mixture was stirred at room temperature for 24 hours. 2M LiOH.H2O in water (3 mL) was then added and stirred for 30 minutes. The precipitate formed was filtered, washed with CH2Cl2 (3×2 mL), and dried to provide N-(5-bromo-4-fluoro-1H-pyrrolo[2,3-b]pyridin-3-yl)-3-methoxypropanamide (115 mg, 42% yield) as a solid. 1H NMR (400 MHz, (CD3)2SO) δ 12.05 (br s, 1H), 9.55 (s, 1H), 8.34 (d, 1H), 7.63 (s, 1H), 3.63 (t, 2H), 3.26 (s, 3H), 2.58 (t, 2H); LCMS (APCI+) m/z 317.9 (M+H)+, Retention time=2.57 minutes (Method 2).

Workup

  1. stirringstirred for 30 minutes
  2. customThe precipitate formed
  3. filtrationwas filtered
  4. washwashed with CH2Cl2 (3×2 mL)
  5. customdried

Sources & evidence

ORD record
ord-8870781a87f24355aca9cf853ccc69b8
Source dataset
uspto-grants-2014_06
Patent number
US08758830B2

Reaction notes

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