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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
ノート
印刷プレビュー

反応式

HRID 18327 の反応式
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
参加物実験手順後処理出典と根拠反応ノート

参加物

8

反応物 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

生成物 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
収率 25%

試薬・触媒・溶媒 2

HCID 962Water溶媒2 回HCID 6228Dimethylformamide溶媒

実験手順

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)+.

後処理

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

出典と根拠

ORDレコード
ord-ed386be55d6b4488bd58e9a57fddd2c9
出典データセット
uspto-grants-2010_06
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07741339B2

反応ノート

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