Ethylamine → HCID 86677698, compound

HRID 1499766Notes

Reaction equation

HRID 1499766 reaction equation
[C:1]([C:4]1[C:5]([O:15][CH2:16][CH3:17])=[C:6]([C:10]([CH3:14])=[C:11]([Cl:13])[CH:12]=1)[C:7]([OH:9])=O)(=[O:3])[CH3:2].F[P-](F)(F)(F)(F)F.[N:25]1(O[P+](N(C)C)(N(C)C)N(C)C)[C:29]2C=CC=C[C:28]=2N=N1.C(N(CC)C(C)C)(C)C.C(N)C.C1COCC1>CN(C)C=O.O>[C:1]([C:4]1[C:5]([O:15][CH2:16][CH3:17])=[C:6]([C:10]([CH3:14])=[C:11]([Cl:13])[CH:12]=1)[C:7]([NH:25][CH2:29][CH3:28])=[O:9])(=[O:3])[CH3:2]

Participants

8

Reactant 5

HCID 6341EthylamineHCID 8028TetrahydrofuranHCID 81531DiisopropylethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 86677697HCID 86677697, compound

Product 1

HCID 86677698HCID 86677698, compoundYield 70.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 3-acetyl-5-chloro-2-ethoxy-6-methylbenzoic acid (0.26 g, 1.0 mmol) in N,N-dimethylformamide (5 mL)was added benzotriazol-1-yloxytris(dimethylamino)phosphonium hexafluorophosphate (0.67 g, 1.5 mmol). After stirring for 10 min, N,N-diisopropylethylamine (0.35 mL, 2.0 mmol) and 2.0 M ethylamine in THF (2.5 mL, 5.1 mmol) was added. The resulting mixture was stirred at room temperature for 2 h. The reaction solution was diluted with water, and extracted with dichloromethane. The combined organic layers were concentrated and purified on silica gel column (eluting with 0% to 50% EtOAc in hexanes) to give the desired product (0.2 g, 70%). LCMS calculated for C14H19ClNO3 (M+H)+: m/z=284.1; Found: 284.1.

Workup

  1. stirringThe resulting mixture was stirred at room temperature for 2 h
  2. extractionextracted with dichloromethane
  3. concentrationThe combined organic layers were concentrated
  4. custompurified on silica gel column (eluting with 0% to 50% EtOAc in hexanes)

Sources & evidence

ORD record
ord-d5cdc990563a437483d69467384911dc
Source dataset
uspto-grants-2015_12
Patent number
US09199982B2

Reaction notes

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