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

HRID 415310ノート

反応式

HRID 415310 の反応式
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

参加物

7

反応物 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

生成物 1

HCID 90970678Benzo[d]oxazole-7-carboxamide収率 7%

試薬・触媒・溶媒 1

HCID 20976018Dichloride methane溶媒

実験手順

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)+.

後処理

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

出典と根拠

ORDレコード
ord-d4a18c09fb3b4217aacbe169d92f4a22
出典データセット
uspto-grants-2012_01
特許番号
US08088760B2

反応ノート

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