Ammonia → 3-{4-[(3-Fluorophenyl)methoxy]phenyl}prop-2-ynamide

HRID 2184355Notes

Reaction equation

HRID 2184355 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:18]=[CH:19][CH:20]=1)[CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]#[C:14][C:15](O)=[O:16])=[CH:9][CH:8]=1.O[N:22]1C2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC.N>C1COCC1.O>[F:1][C:2]1[CH:3]=[C:4]([CH:18]=[CH:19][CH:20]=1)[CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]#[C:14][C:15]([NH2:22])=[O:16])=[CH:9][CH:8]=1

Participants

7

Reactant 4

HCID 222AmmoniaHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 692917433-{4-[(3-Fluorophenyl)methoxy]phenyl}prop-2-ynoic acid

Product 1

HCID 692892093-{4-[(3-Fluorophenyl)methoxy]phenyl}prop-2-ynamideYield 59%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

50 mg (0.19 mmol) of [4-(3-fluoro-benzyloxy)-phenyl]-propynoic acid is dissolved in 3 ml of THF and treated with 27 mg (0.2 mmol) of 1-hydroxybenzotriazole and 37 mg (0.19 mmol) of N-(3-dimethylaminopropyl)-N′-ethyl-carbodiimide hydrochloride. The resulting mixture is stirred at RT for 30 minutes, cooled to 0° C. and treated with 1 ml of concentrated ammonia. The suspension is stirred overnight at RT, diluted with water and extracted three times with dichloromethane. Flash-chromatography (silica gel, dichloromethane/methanol) yields 29 mg (59%) of a colorless solid. MS: m/e=270.2 (M++H).

Workup

  1. temperaturecooled to 0° C.
  2. stirringThe suspension is stirred overnight at RT
  3. extractionextracted three times with dichloromethane

Sources & evidence

ORD record
ord-7e8659282a694a2391809885b9e3db2c
Source dataset
uspto-grants-2005_05
Patent number
US06900354B2

Reaction notes

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