N,N-Dimethylglycine → Benzo[d]oxazole-7-carboxamide

HRID 415310Notes

Reaction equation

HRID 415310 reaction equation
N1CCCC([C:7]2[O:8][C:9]3[C:15]([C:16]([NH2:18])=[O:17])=[CH:14][CH:13]=[CH:12][C:10]=3[N:11]=2)C1.Cl.C(N=C=NCCCN(C)C)C.ON1C2C=CC=CC=2N=N1.C(N(CC)CC)C.CN(C)CC(O)=O>C.[Cl-].[Cl-]>[O:8]1[C:9]2[C:15]([C:16]([NH2:18])=[O:17])=[CH:14][CH:13]=[CH:12][C:10]=2[N:11]=[CH:7]1

Participants

7

Reactant 5

HCID 673N,N-DimethylglycineHCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 666209242-(Piperidin-3-yl)benzo[d]oxazole-7-carboxamide

Product 1

HCID 90970678Benzo[d]oxazole-7-carboxamideYield 7%

Reagents, catalysts & solvents 1

HCID 20976018Dichloride methaneSolvent

Procedure

A mixture of 2-(piperidin-3-yl)benzo[d]oxazole-7-carboxamide (160 mg, 1.2 mmol), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (82.4 mg, 0.61 mmol), 1-hydroxybenzotriazole (82 mg, 0.61 mmol), triethyl amine (117 mg, 0.61 mmol), 2-(dimethylamino)acetic acid (83 mg, 0.61 mmol) were added in 50 ml dichloride methane and stirred at room temperature over night. The mixture was evaporated under reduced pressure and purified by pre-HPLC. 13 mg 2-(1-(2-dimethylamino)acetyl)piperidin-3-yl)benzo[d]oxazole-7-carboxamide was obtained. Yield 7%. 1H-NMR (400 MHz, CD3OD): δ 1.52-1.65 (m, 1H), 1.77-1.85 (m, 1H), 2.15-2.31 (m, 8H), 2.20-2.28 (m, 2H), 3.31-3.39 (m, 2H), 3.75-3.90 (m, 2H), 4.42-4.36 (m, 1H), 7.44-7.47 (m, 1H), 7.81-7.88 (m, 2H). LC-MS (ESI) m/z: 331 (M+1)+.

Workup

  1. customThe mixture was evaporated under reduced pressure
  2. custompurified by pre-HPLC

Sources & evidence

ORD record
ord-d4a18c09fb3b4217aacbe169d92f4a22
Source dataset
uspto-grants-2012_01
Patent number
US08088760B2

Reaction notes

Loading…