Ammonia → HCID 59497258, compound

HRID 1747320Notes

Reaction equation

HRID 1747320 reaction equation
[C:1]1([CH2:11][N:12]2[C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=3[N:14]([CH2:21][CH2:22][C:23](O)=[O:24])[C:13]2=[O:26])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.N.O1CCOCC1.O[N:35]1C2C=CC=CC=2N=N1.CN(C)CCCN=C=NCC>O.C1COCC1>[C:1]1([CH2:11][N:12]2[C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=3[N:14]([CH2:21][CH2:22][C:23]([NH2:35])=[O:24])[C:13]2=[O:26])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1

Participants

8

Reactant 5

HCID 222AmmoniaHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 312751,4-DioxaneHCID 757711-HydroxybenzotriazoleHCID 56666721HCID 56666721, compound

Product 1

HCID 59497258HCID 59497258, compoundYield 76.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To the THF (1.0 mL) suspension of 3-(3-Naphthalen-1-ylmethyl-2-oxo-2,3-dihydro-benzimidazol-1-yl)-propionic acid (50 mg, 0.14 mmol) at room temperature are added ammonia 0.5 M solution in dioxane (1.4 mL, 0.72 mmol) and 1-hydroxybenzotriazole (94 mg, 0.7 mmol). Then N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide (118 mg, 0.61 mmol) is added in small portions. The reaction mixture is stirred for 20 hr and then water (5 mL) is added and the mixture is extracted with EtOAc (3×10 mL). The organic layers are combined, dried over MgSO4 and concentrated to give crude product. Purification by preparative TLC using 5% MeOH in CH2Cl2 affords 37 mg (74%) of 3-(3-Naphthalen-1-ylmethyl-2-oxo-2,3-dihydro-benzimidazol-1-yl)-propionamide. LCMS (ESMS): m/z 346.12 (M+H+).

Workup

  1. extractionthe mixture is extracted with EtOAc (3×10 mL)
  2. dry with materialdried over MgSO4
  3. concentrationconcentrated
  4. customto give crude product
  5. customPurification by preparative TLC

Sources & evidence

ORD record
ord-3cd6a9103bf2412d8d224a05657fc33c
Source dataset
uspto-grants-2015_10
Patent number
US09150556B2

Reaction notes

Loading…