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

HRID 452270Notes

Reaction equation

HRID 452270 reaction equation
CC1(C)C[CH:10]([NH2:12])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7]C=2)[O:3]1.[N:14]1[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH:17]=[CH:16][C:15]=1/[CH:24]=[CH:25]/[C:26]([OH:28])=O.CCN=C=NCCCN(C)C.[ClH:40].[CH:41]1[CH:42]=[CH:43][C:44]2N(O)N=N[C:45]=2[CH:46]=1.C(N(CC)CC)C>ClCCl>[Cl:40][C:41]1[CH:46]=[C:45]2[C:44](=[CH:43][CH:42]=1)[O:3][C:4]1([CH2:5][CH2:6][CH2:7]1)[CH2:9][CH:10]2[NH:12][C:26](=[O:28])/[CH:25]=[CH:24]/[C:15]1[CH:16]=[CH:17][C:18]2[C:23](=[CH:22][CH:21]=[CH:20][CH:19]=2)[N:14]=1

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 7129193-(2-Quinolinyl)-2-propenoic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 153387052,2-dimethyl-3,4-dihydro-2H-1-benzopyran-4-amine

Product 1

HCID 68790685(2E)-N-(6-Chloro-3,4-dihydrospiro[chromene-2,1'-cyclobutan]-4-yl)-3-quinolin-2-ylacrylamideYield 46.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

This compound was prepared from Intermediate 2 (200 mg, 0.894 mmol) and (2E)-3-quinolin-2-ylacrylic acid (213 mg, 1.073 mmol) in presence of EDCI.HCl (257 mg, 1.342 mmol), HOBt (205 mg, 1.342 mmol) and triethylamine (248 μl, 2.684 mmol) in dichloromethane (10 ml) as described in Example 1 to give 167 mg of the product as a white solid; 1H NMR (300 MHz, DMSO-d6) δ 1.69-1.92 (m, 3H), 2.04-2.16 (m, 3H), 2.27-2.41 (m, 2H), 5.20 (q, J=10.2 Hz, 1H), 6.81 (d, J=9.0 Hz, 1H), 7.10-7.20 (m, 2H), 7.27 (d, J=15.6 Hz, 1H), 7.60 (t, J=7.8 Hz, 1H), 7.73-7.77 (m, 2H), 7.92-7.99 (m, 2H), 8.29 (s, 1H), 8.40 (d, J=8.1 Hz, 1H), 8.88 (d, J=8.4 Hz, 1H).

Sources & evidence

ORD record
ord-c4aae4a288534859969b5d1a812c525f
Source dataset
uspto-grants-2013_07
Patent number
US08487121B2

Reaction notes

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