Triethylamine → (2E)-2-(6-Chloro-3,4-dihydrospiro[chromene-2,1'-cyclobutan]-4-ylidene)-N-[2-(cyclopentyloxy)phenyl]acetamide

HRID 453932

反応式

HRID 453932 の反応式
[Cl:1][C:2]1[CH:3]=[C:4]2[C:12](=[CH:13][CH:14]=1)[O:11][C:7]1([CH2:10][CH2:9][CH2:8]1)[CH2:6]/[C:5]/2=[CH:15]\[C:16](OCC)=[O:17].[CH:21]1([O:26][C:27]2[CH:33]=[CH:32][CH:31]=[CH:30][C:28]=2[NH2:29])[CH2:25][CH2:24][CH2:23][CH2:22]1.CCN=C=NCCCN(C)C.Cl.C1C=CC2N(O)N=NC=2C=1.C(N(CC)CC)C>ClCCl>[Cl:1][C:2]1[CH:3]=[C:4]2[C:12](=[CH:13][CH:14]=1)[O:11][C:7]1([CH2:10][CH2:9][CH2:8]1)[CH2:6]/[C:5]/2=[CH:15]\[C:16]([NH:29][C:28]1[CH:30]=[CH:31][CH:32]=[CH:33][C:27]=1[O:26][CH:21]1[CH2:25][CH2:24][CH2:23][CH2:22]1)=[O:17]

参加物

7

反応物 5

HCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 64853982-(Cyclopentyloxy)anilineHCID 86652760Ethyl (2E)-(6-chlorospiro[chromene-2,1'-cyclobutan]-4(3H)-ylidene)acetate2 回

生成物 1

HCID 58237898(2E)-2-(6-Chloro-3,4-dihydrospiro[chromene-2,1'-cyclobutan]-4-ylidene)-N-[2-(cyclopentyloxy)phenyl]acetamide

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

The title compound was prepared by the coupling ethyl (2E)-(6-chlorospiro[chromene-2,1′-cyclobutan]-4(3H)-ylidene)acetate (Step 2 of Intermediate 1) with 2-(cyclopentyloxy)aniline (120 mg, 0.681 mmol) (150 mg, 0.565 mmol) in presence of EDCI.HCl (163 mg, 0.851 mmol), HOBt (130 mg, 0.851 mmol) and triethylamine (157 μl, 1.134 mmol) in dichloromethane (5 ml) as described in Method A to give 95 mg of the product as a white solid; 1H NMR (300 MHz, CDCl3) δ 1.53-1.65 (m, 8H), 1.74-1.90 (m, 4H), 2.22-2.30 (m, 2H), 2.47-2.57 (m, 2H), 3.50 (s, 2H), 4.67 (br s, 1H), 6.75 (d, J=8.1 Hz, 2H), 6.85-6.96 (m, 2H), 7.04-7.10 (m, 2H), 8.32 (d, J=7.8 Hz, 1H).

出典と根拠

ORDレコード
ord-64794c33638a4227b6dc18afbc65b0bd
出典データセット
uspto-grants-2013_07
特許番号
US08492568B2

関連ノート

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