Triethylamine → HCID 59255329, compound

HRID 78270Notes

Reaction equation

HRID 78270 reaction equation
[C:1]([C:3]1[C:4]([NH2:10])=[N:5][C:6]([NH2:9])=[CH:7][CH:8]=1)#[CH:2].[F:11][C:12]1[CH:28]=[CH:27][C:15]([CH2:16][C:17]2[O:21][C:20]([CH2:22][C:23](Cl)=[N:24][OH:25])=[CH:19][CH:18]=2)=[CH:14][CH:13]=1.C(N(CC)CC)C>O1CCCC1>[F:11][C:12]1[CH:28]=[CH:27][C:15]([CH2:16][C:17]2[O:21][C:20]([CH2:22][C:23]3[CH:2]=[C:1]([C:3]4[C:4]([NH2:10])=[N:5][C:6]([NH2:9])=[CH:7][CH:8]=4)[O:25][N:24]=3)=[CH:19][CH:18]=2)=[CH:14][CH:13]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 552816763-Ethynylpyridine-2,6-diamineHCID 72262865(5-(4-Fluorobenzyl)-furan-2-yl)acetohydroximoyl chloride

Product 1

HCID 59255329HCID 59255329, compoundYield 33%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a tetrahydrofuran (3 mL) solution of 3-ethynyl-pyridin-2,6-diamine (50 mg, 0.376 mmol) described in Manufacturing Example 13-1-3 and (5-(4-fluorobenzyl)-furan-2-yl)acetohydroximoyl chloride (161 mg, 0.602 mmol) described in Manufacturing Example 208-1-5 was added triethylamine (131 μL, 0.94 mmol), which was stirred for 19 hours at room temperature. This mixture was partitioned into ethyl acetate and water. The organic layer was separated, washed with water and saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate, and filtered. The filtrate was concentrated under a reduced pressure, and the residue was purified by NH silica gel column chromatography (ethyl acetate:heptane=1:1, then ethyl acetate) to obtain the title compound (45 mg, 33%).

Workup

  1. customThis mixture was partitioned into ethyl acetate and water
  2. customThe organic layer was separated
  3. washwashed with water and saturated aqueous sodium chloride
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated under a reduced pressure
  7. customthe residue was purified by NH silica gel column chromatography (ethyl acetate

Sources & evidence

ORD record
ord-8b790e6580264ba4aa6238fd0a91fa97
Source dataset
uspto-grants-2014_09
Patent number
US08841327B2

Reaction notes

Loading…