Diisopropylethylamine → (E)-N-(3-Chloro-2-ethoxybenzyl)-N-methyl-3-(7-oxo-5,6,7,8-tetrahydro-[1,8]naphthyridin-3-yl)acrylamide

HRID 2097017노트

반응식

HRID 2097017 반응식
[Cl:1][C:2]1[C:3]([O:11][CH:12]([CH3:14])C)=[C:4]([CH:8]=[CH:9][CH:10]=1)[CH2:5]CN.[CH:15]([N:18](C(C)C)CC)(C)C.Cl.[O:25]=[C:26]1[NH:35][C:34]2[N:33]=[CH:32][C:31](/[CH:36]=[CH:37]/[C:38]([OH:40])=O)=[CH:30][C:29]=2[CH2:28][CH2:27]1.O.ON1C2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC>CN(C=O)C.O>[Cl:1][C:2]1[C:3]([O:11][CH2:12][CH3:14])=[C:4]([CH:8]=[CH:9][CH:10]=1)[CH2:5][N:18]([CH3:15])[C:38](=[O:40])/[CH:37]=[CH:36]/[C:31]1[CH:32]=[N:33][C:34]2[NH:35][C:26](=[O:25])[CH2:27][CH2:28][C:29]=2[CH:30]=1

참가 물질

8

반응물 5

HCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 66905305(E)-3-(7-oxo-5,6,7,8-tetrahydro-1,8-naphthyridin-3-yl)acrylic Acid HydrochlorideHCID 66967106(3-Chloro-2-isopropoxybenzyl)methylamine

생성물 1

HCID 16662047(E)-N-(3-Chloro-2-ethoxybenzyl)-N-methyl-3-(7-oxo-5,6,7,8-tetrahydro-[1,8]naphthyridin-3-yl)acrylamide수율 21.7%

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

실험 절차

A stirring solution of (3-chloro-2-isopropoxybenzyl)methylamine (0.229 g, 1.07 mmol) and diisopropylethylamine (0.51 mL, 2.9 mmol) in DMF (20 mL) under N2 was treated sequentially with (E)-3-(7-oxo-5,6,7,8-tetrahydro-[1,8]naphthyridin-3-yl)acrylic acid hydrochloride (0.250 g, 0.980 mmol), 1-hydroxybenzotriazole hydrate (0.144 g, 1.07 mmol) and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (0.205 g, 1.07 mmol). After stirring for 18 h, the reaction mixture was diluted with H2O (30 mL). The resulting solids were collected by filtration and washed with Et2O (100 mL), suspended in MeOH (30 mL) and sonicated for 30 minutes. The solids were then collected by filtration, washed with MeOH and dried to yield the title compound (0.085 g, 21%) as a white solid and as a mixture of amide rotamers: 1H NMR (300 MHz, DMSO-d6) δ 10.67-10.64 (m, 1H), 8.37-8.32 (m, 1H), 8.09-7.91 (m, 1H), 7.53-7.48 (m, 1H), 7.42-7.37 (m, 1H), 7.28-7.02 (m, 3H), 4.83-4.68 (m, 2H), 4.53-4.45 (m, 1H), 2.94-2.85 (m, 5H), 2.56-2.49 (m, 2H), 1.33-1.28 (m, 6H); MS (ESI) m/e 414 (M+H)+.

후처리

  1. filtrationThe resulting solids were collected by filtration
  2. washwashed with Et2O (100 mL)
  3. customsonicated for 30 minutes
  4. filtrationThe solids were then collected by filtration
  5. washwashed with MeOH
  6. customdried

출처 및 근거

ORD 기록
ord-c85a261020ea41c1b6ce255ef5f9eaab
출처 데이터셋
uspto-grants-2013_05
특허 번호
US08450307B2

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