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1,2-Dichloroethane → (E)-N-(2,3-dihydro-1H-3a-azacyclopenta[a]indene-8-ylmethyl)-N-methyl-3-(7-oxo-5,6,7,8-tetrahydro-1,8-naphthyridin-3-yl)acrylamide

HRID 18327
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HRID 18327 반응식
C(Cl)CCl.Cl.[O:6]=[C:7]1[NH:16][C:15]2[N:14]=[CH:13][C:12](/[CH:17]=[CH:18]/[C:19]([OH:21])=O)=[CH:11][C:10]=2[CH2:9][CH2:8]1.[CH3:22][NH:23][CH2:24][C:25]1[C:33]2[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=2[N:27]2[CH2:34][CH2:35][CH2:36][C:26]=12.C1C=CC2N(O)N=NC=2C=1.CCN(CC)CC>CN(C=O)C.O>[CH2:36]1[C:26]2=[C:25]([CH2:24][N:23]([CH3:22])[C:19](=[O:21])/[CH:18]=[CH:17]/[C:12]3[CH:13]=[N:14][C:15]4[NH:16][C:7](=[O:6])[CH2:8][CH2:9][C:10]=4[CH:11]=3)[C:33]3[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=3[N:27]2[CH2:34][CH2:35]1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

8

반응물 5

HCID 111,2-DichloroethaneHCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 221390482,3-dihydro-8-(methylaminomethyl)-1H-3a-azacyclopenta[a]indeneHCID 66905305(E)-3-(7-oxo-5,6,7,8-tetrahydro-1,8-naphthyridin-3-yl)acrylic Acid Hydrochloride

생성물 1

HCID 10092390
(E)-N-(2,3-dihydro-1H-3a-azacyclopenta[a]indene-8-ylmethyl)-N-methyl-3-(7-oxo-5,6,7,8-tetrahydro-1,8-naphthyridin-3-yl)acrylamide
수율 25%

시약·촉매·용매 2

HCID 962Water용매2회HCID 6228Dimethylformamide용매

실험 절차

EDC (0.192 g, 1.0 mmole) was added to a solution of (E)-3-(7-oxo-5,6,7,8-tetrahydro-1,8-naphthyridin-3-yl)acrylic acid hydrochloride salt (0.254 g, 1.0 mmole), 2,3-dihydro-8-(methylaminomethyl)-1H-3a-azacyclopenta[a]indene (0.2 g, 1.0 mmole), HOBt. H2O (0.135 g, 1.0 mmole), and Et3N (0.15 mL, 1.1 mmole) in DMF (20 mL) at RT. The reaction was stirred overnight, then was poured into H2O (50 mL) and extracted with CH2Cl2 (2×30 mL). The combined extracts were washed with brine and dried (MgSO4). Flash chromatography on silica gel (5% MeOH/CH2Cl2) gave the title compound (0.1 g, 25%) a yellow solid: MS (ES) m/e 401 (M+H)+.

후처리

  1. customat RT
  2. extractionextracted with CH2Cl2 (2×30 mL)
  3. washThe combined extracts were washed with brine
  4. dry with materialdried (MgSO4)

출처 및 근거

ORD 기록
ord-ed386be55d6b4488bd58e9a57fddd2c9
출처 데이터셋
uspto-grants-2010_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07741339B2

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