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(3,4-Dimethoxyphenyl)acetic acid → N-(6-Chloro-3,4-dihydrospiro[chromene-2,1'-cyclobutan]-4-yl)-2-(3,4-dimethoxyphenyl)acetamide

HRID 452253
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HRID 452253 반응식
CC1(C)C[CH:10]([NH2:12])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7]C=2)[O:3]1.[CH3:14][O:15][C:16]1[CH:17]=[C:18]([CH2:24][C:25]([OH:27])=O)[CH:19]=[CH:20][C:21]=1[O:22][CH3:23].CCN=C=NCCCN(C)C.[ClH:39].[CH:40]1[CH:41]=[CH:42][C:43]2N(O)N=N[C:44]=2[CH:45]=1.C(N(CC)CC)C>ClCCl>[Cl:39][C:40]1[CH:45]=[C:44]2[C:43](=[CH:42][CH:41]=1)[O:3][C:4]1([CH2:5][CH2:6][CH2:7]1)[CH2:9][CH:10]2[NH:12][C:25](=[O:27])[CH2:24][C:18]1[CH:19]=[CH:20][C:21]([O:22][CH3:23])=[C:16]([O:15][CH3:14])[CH:17]=1
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참가 물질

7

반응물 5

HCID 7139(3,4-Dimethoxyphenyl)acetic acidHCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 153387052,2-dimethyl-3,4-dihydro-2H-1-benzopyran-4-amine

생성물 1

HCID 44132276
N-(6-Chloro-3,4-dihydrospiro[chromene-2,1'-cyclobutan]-4-yl)-2-(3,4-dimethoxyphenyl)acetamide

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

The title compound was prepared from Intermediate 2 (200 mg, 0.763 mmol) and 3,4-dimethoxyphenylacetic acid (224 mg, 1.145 mmol) in presence of EDCI.HCl (219 mg, 1.145 mmol), HOBt (175 mg, 1.145 mmol) and triethylamine (425 μl, 3.053 mmol) in dichloromethane (10 ml) as described in Example 1 to give 217 mg of the product as a white solid; IR (KBr) 3232, 2938, 1634, 1478, 1241, 813 cm−1; 1H NMR (300 MHz, CDCl3) δ 1.62-1.70 (m, 2H), 1.87-1.90 (m, 2H), 1.99-2.15 (m, 2H), 2.18-2.37 (m, 2H), 3.60 (q, J=16.2 Hz, 2H), 3.85 (s, 6H), 5.23 (q, J=9.6 Hz, 1H), 5.48 (d, J=9.0 Hz, 1H), 6.68 (d, J=9.0 Hz, 1H), 6.77-6.84 (m, 3H), 6.96 (s, 1H), 7.04 (d, J=8.4 Hz, 1H); ESI-MS (m/z) 401.27 (100%).

출처 및 근거

ORD 기록
ord-a362e89873744c2ba75f0d3ac6d270da
출처 데이터셋
uspto-grants-2013_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08487121B2

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