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

HRID 415310노트

반응식

HRID 415310 반응식
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

참가 물질

7

반응물 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

생성물 1

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

시약·촉매·용매 1

HCID 20976018Dichloride methane용매

실험 절차

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)+.

후처리

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

출처 및 근거

ORD 기록
ord-d4a18c09fb3b4217aacbe169d92f4a22
출처 데이터셋
uspto-grants-2012_01
특허 번호
US08088760B2

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