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

HRID 452268노트

반응식

HRID 452268 반응식
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

참가 물질

7

반응물 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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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)+.

출처 및 근거

ORD 기록
ord-ca1ed5624ea0447bbed871dbcd618669
출처 데이터셋
uspto-grants-2013_07
특허 번호
US08487121B2

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