Diisopropylethylamine → HCID 70921731, compound

HRID 2069125Notes

Reaction equation

HRID 2069125 reaction equation
[CH3:1][C:2]1[CH:15]=[C:14]([N+:16]([O-:18])=[O:17])[CH:13]=[CH:12][C:3]=1[O:4][C:5]1[CH:10]=[CH:9][N:8]=[C:7]([NH2:11])[CH:6]=1.[CH3:19][O:20][CH2:21][C:22](Cl)=[O:23].CCN(C(C)C)C(C)C>C1COCC1>[CH3:19][O:20][CH2:21][C:22]([NH:11][C:7]1[CH:6]=[C:5]([O:4][C:3]2[CH:12]=[CH:13][C:14]([N+:16]([O-:18])=[O:17])=[CH:15][C:2]=2[CH3:1])[CH:10]=[CH:9][N:8]=1)=[O:23]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 96623Methoxyacetyl chlorideHCID 231530654-(2-Methyl-4-nitrophenoxy)pyridin-2-amine

Product 1

HCID 70921731HCID 70921731, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of 4-(2-methyl-4-nitrophenoxy)pyridin-2-amine [WO2007059257] (405 mg, 1.65 mmol) in THF (5.0 mL) at 0° C. was added 2-methoxyacetyl chloride (604 μL, 6.61 mmol) and DIPEA (1.44 mL, 8.26 mmol) and the reaction mixture warmed to RT for 30 min. The reaction was quenched by addition of a 1% solution of NH3 in MeOH (3.0 mL) and was kept at RT for 16 hr. A second aliquot of a solution of NH3 in MeOH (7M, 1.0 mL) was added and after 30 min at RT the resulting mixture was evaporated in vacuo. The residue was subjected to SCX capture and release to afford 2-methoxy-N-(4-(2-methyl-4-nitrophenoxy)pyridin-2-yl)acetamide as an orange oil (357 mg, 92% pure, 63%); Rt 2.07 min (Method 2); m/z 318 (M+H)+ (ES+), which was used directly in the next step (below).

Workup

  1. customThe reaction was quenched by addition of a 1% solution of NH3 in MeOH (3.0 mL)
  2. additionA second aliquot of a solution of NH3 in MeOH (7M, 1.0 mL) was added and after 30 min at RT the resulting mixture
  3. customwas evaporated in vacuo

Sources & evidence

ORD record
ord-e11dfec183004ae7ae078825c73b451d
Source dataset
uspto-grants-2012_10
Patent number
US08299074B2

Reaction notes

Loading…