1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → (E)-3-(2,2-Dimethyl-3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazin-7-yl)-N-(3-methoxy-2-propoxy-benzyl)-N-methyl-acrylamide

HRID 2097135노트

반응식

HRID 2097135 반응식
[CH3:1][O:2][C:3]1[C:4]([O:12][CH2:13][CH2:14][CH3:15])=[C:5]([CH:9]=[CH:10][CH:11]=1)[CH2:6][NH:7][CH3:8].[CH3:16][C:17]1([CH3:33])[O:22][C:21]2[CH:23]=[C:24]([CH:27]=[CH:28][C:29]([OH:31])=O)[CH:25]=[N:26][C:20]=2[NH:19][C:18]1=[O:32].ON1C2C=CC=CC=2N=N1.C(N(C(C)C)CC)(C)C.CN(C)CCCN=C=NCC>CN(C=O)C.O>[CH3:33][C:17]1([CH3:16])[O:22][C:21]2[CH:23]=[C:24](/[CH:27]=[CH:28]/[C:29]([N:7]([CH2:6][C:5]3[CH:9]=[CH:10][CH:11]=[C:3]([O:2][CH3:1])[C:4]=3[O:12][CH2:13][CH2:14][CH3:15])[CH3:8])=[O:31])[CH:25]=[N:26][C:20]=2[NH:19][C:18]1=[O:32]

참가 물질

8

반응물 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 28338626(3-Methoxy-2-propoxybenzyl)methylamineHCID 669676363-(2,2-dimethyl-3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazin-7-yl)-acrylic acid

생성물 1

HCID 16660813(E)-3-(2,2-Dimethyl-3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazin-7-yl)-N-(3-methoxy-2-propoxy-benzyl)-N-methyl-acrylamide수율 75%

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

실험 절차

To a solution of (3-methoxy-2-propoxy-benzyl)-methyl-amine (115 mg, 0.55 mmol) in DMF (5 mL) were added in sequential order 3-(2,2-dimethyl-3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazin-7-yl)-acrylic acid (181 mg, 0.5 mmol), 1-hydroxybenzotriazole (74 mg, 0.55 mmol), diisopropylethylamine (261 uL, 1.5 mmol), and N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide (110 mg, 0.55 mmol). The reaction was placed in a microwave at 130° C. for 5 min. The solution was cooled in an ice bath and water was added with rapid stirring. The precipitate was filtered, dried and triturated with diethyl ether to yield the title compound (164 mg, 75%) as a white solid and as a mixture of amide rotomers: 1H NMR (400 MHz, DMSO-d6) δ 11.37-11.39 (m, 1H), 8.14-8.18 (m, 1H), 7.87-7.93 (m, 1H), 7.47-7.53 (m, 1H), 7.27-7.34 (m, 1H), 6.92-7.09 (m, 3H), 6.60-6.66 (m, 1H), 4.62-4.79 (m, 2H), 3.84-3.90 (m, 2H), 3.78 (s, 3H), 2.88-3.09 (m, 3H), 1.70-1.74 (m, 2H), 1.40-1.49 (m, 6H), 0.93-0.99 (m, 3H); MS (ESI) m/e 440 (C24H29N3O5+H)+.

후처리

  1. temperatureThe solution was cooled in an ice bath
  2. filtrationThe precipitate was filtered
  3. customdried
  4. customtriturated with diethyl ether

출처 및 근거

ORD 기록
ord-0e14159d98a4470da6a17d413883e0a5
출처 데이터셋
uspto-grants-2013_05
특허 번호
US08450307B2

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