Triethylamine → N-(6-Chloro-3,4-dihydrospiro[chromene-2,1'-cyclobutan]-4-yl)-3-(1-naphthyl)-propanamide

HRID 452268ノート

反応式

HRID 452268 の反応式
C[C:2]1([CH3:13])[CH2:11][CH:10](N)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[O:3]1.[C:14]1([CH:24]([CH3:28])C(O)=O)[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH:17]=[CH:16][CH:15]=1.CCN=C=NCCCN(C)C.[ClH:40].C1C=CC2N([OH:50])N=NC=2C=1.C([N:53]([CH2:56][CH3:57])[CH2:54]C)C>ClCCl>[Cl:40][C:7]1[CH:8]=[C:9]2[C:4](=[CH:5][CH:6]=1)[O:3][C:2]1([CH2:11][CH2:10][CH2:13]1)[CH2:57][CH:56]2[NH:53][C:54](=[O:50])[CH2:28][CH2:24][C:14]1[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH:17]=[CH:16][CH:15]=1

参加物

7

反応物 5

HCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 1227522-(Naphthalen-1-yl)propanoic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 153387052,2-dimethyl-3,4-dihydro-2H-1-benzopyran-4-amine

生成物 1

HCID 44133803N-(6-Chloro-3,4-dihydrospiro[chromene-2,1'-cyclobutan]-4-yl)-3-(1-naphthyl)-propanamide

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

The title compound was prepared from Intermediate 2 (200 mg, 0.896 mmol) and 1-naphthylpropanoic acid (178 mg, 0.896 mmol) in presence of EDCI.HCl (256 mg, 1.345 mmol), HOBt (205 mg, 1.345 mmol) and triethylamine (371 μl, 2.690 mmol) in dichloromethane (10 ml) as described in Example 1 to give 160 mg of the product as a white solid; 1H NMR (300 MHz, CDCl3) δ 1.43-1.51 (m, 1H), 1.63-1.69 (m, 1H), 1.81-1.97 (m, 2H), 2.09-2.26 (m, 4H), 2.64-2.70 (m, 2H), 3.50 (t, J=7.2 Hz, 2H), 5.14 (q, J=9.9 Hz, 1H), 5.26 (d, J=8.4 Hz, 1H), 6.65 (d, J=8.7 Hz, 1H), 6.82 (s, 1H), 7.01 (dd, J=2.4, 8.7 Hz, 1H), 7.35-7.54 (m, 4H), 7.73 (d, J=6.9 Hz, 1H), 7.84 (d, J=7.5 Hz, 1H), 8.04 (d, J=8.1 Hz, 1H); ESI-MS (m/z) 406.34 (M+H)+.

出典と根拠

ORDレコード
ord-ca1ed5624ea0447bbed871dbcd618669
出典データセット
uspto-grants-2013_07
特許番号
US08487121B2

反応ノート

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