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1,2-Dichloroethane → (e)-n-((3,6-Dimethyl-1h-indol-5-yl)methyl)-n-methyl-3-(3-oxo-3,4-dihydro-2h-pyrido[3,2-b][1,4]oxazin-yl)acrylamide

HRID 2097201
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HRID 2097201 반응식
[CH2:1](Cl)[CH2:2]Cl.CC[C:7]1[C:12]2[NH:13][C:14](CN)=[C:15]([CH3:16])[C:11]=2[CH:10]=[CH:9][CH:8]=1.Cl.[O:20]=[C:21]1[CH2:26][O:25][C:24]2[CH:27]=[C:28](/C=C/C(O)=O)[CH:29]=[N:30][C:23]=2[NH:22]1.[CH3:36][CH2:37]N(C(C)C)C(C)C.[CH3:45][N:46]([CH:48]=[O:49])C>O>[CH3:16][C:15]1[C:11]2[C:12](=[CH:7][C:1]([CH3:2])=[C:9]([CH2:8][N:46]([CH3:45])[C:48](=[O:49])/[CH:36]=[CH:37]/[CH:26]3[O:25][C:24]4[CH:27]=[CH:28][CH:29]=[N:30][C:23]=4[NH:22][C:21]3=[O:20])[CH:10]=2)[NH:13][CH:14]=1
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참가 물질

7

반응물 5

HCID 111,2-DichloroethaneHCID 6228DimethylformamideHCID 81531DiisopropylethylamineHCID 66967073(E)-3-(3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazin-7-yl)acrylic acid hydrochlorideHCID 66967213(7-Ethyl-3-methyl-1h-indol-2-yl)-n-methanamine

생성물 1

HCID 87218141
(e)-n-((3,6-Dimethyl-1h-indol-5-yl)methyl)-n-methyl-3-(3-oxo-3,4-dihydro-2h-pyrido[3,2-b][1,4]oxazin-yl)acrylamide

시약·촉매·용매 1

HCID 962Water용매2회

실험 절차

EDC (198 mg, 1.0 mmol) was added to a solution of (7-ethyl-3-methyl-1H-indol-2-yl)-N-methanamine (150 mg, 0.8 mmol), (E)-3-(3-oxo-3,4,dihydro-2H-pyrido[3,2-b][1,4]oxazin-7-yl)acrylic acid hydrochloride (224 mg, 0.87 mmol) HOBT.H2O (107 mg, 0.8 mmol) and DIPEA (0.57 mL, 3.1 mmol) in dry DMF (5 mL). After heating overnight, water was added. The precipitate that formed was washed with ethyl acetate and dried (184 mg, 59%). 1H NMR (300 MHz, DMSO-d6) δ, 11.42 (s, 1H), 10.45 (s, 1H), 8.24-8.05 (rotamers, s, 1H), 7.98-7.80 (rotamers, s, 2H), 7.54 (d, J=7.4 Hz, 1H), 7.24 (m, 1H), 7.14 (m, 1H), 6.98 (s, 1H), 4.90-4.78 (rotamers, s, 2H), 3.05 (s, 2H), 2.84 (s, 3H), 2.45 (s, 3H), 2.31 (s, 3H); m/e 391.1 (C22H22N4O3+H)+.

후처리

  1. temperatureAfter heating overnight
  2. customThe precipitate that formed
  3. washwas washed with ethyl acetate
  4. customdried (184 mg, 59%)

출처 및 근거

ORD 기록
ord-b9c184b6779b4c41b24a89782a6296dc
출처 데이터셋
uspto-grants-2013_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08450307B2

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