Triethylamine → HCID 68792411, compound

HRID 452266Notes

Reaction equation

HRID 452266 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.[CH2:14]([O:21][C:22]1[C:27]([O:28][CH3:29])=[CH:26][CH:25]=[CH:24][C:23]=1/[CH:30]=[CH:31]/[C:32]([OH:34])=O)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.CCN=C=NCCCN(C)C.[ClH:46].[CH:47]1[CH:48]=[CH:49][C:50]2N(O)N=N[C:51]=2[CH:52]=1.C(N(CC)CC)C>ClCCl>[Cl:46][C:47]1[CH:52]=[C:51]2[C:50](=[CH:49][CH:48]=1)[O:3][C:4]1([CH2:5][CH2:6][CH2:7]1)[CH2:9][CH:10]2[NH:12][C:32](=[O:34])/[CH:31]=[CH:30]/[C:23]1[CH:24]=[CH:25][CH:26]=[C:27]([O:28][CH3:29])[C:22]=1[O:21][CH2:14][C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 153387052,2-dimethyl-3,4-dihydro-2H-1-benzopyran-4-amineHCID 19617788HCID 19617788, compound

Product 1

HCID 68792411HCID 68792411, compoundYield 66.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

This compound was prepared from Intermediate 2 (500 mg, 1.938 mmol) and (2E)-3-[2-(benzyloxy)-3-methoxyphenyl]acrylic acid (575 mg, 2.023 mmol) in presence of EDCI.HCl (555 mg, 2.897 mmol), HOBt (443 mg, 2.897 mmol) and triethylamine (806 μl, 5.791 mmol) in dichloromethane (15 ml) as described in Example 1 to give 633 mg of the product as a white solid; 1H NMR (300 MHz, CDCl3) δ 1.70-1.84 (m, 3H), 2.11-2.22 (m, 3H), 2.35-2.47 (m, 2H), 3.89 (s, 3H), 5.02 (q, J=11.4 Hz, 2H), 5.34 (q, J=9.9 Hz, 1H), 5.44 (d, J=8.4 Hz, 1H), 6.59 (d, J=15.6 Hz, 1H), 6.75 (d, J=8.4 Hz, 1H), 6.92-6.96 (m, 1H), 7.04-7.10 (m, 4H), 7.19-7.29 (m, 3H), 7.41 (d, J=6.6 Hz, 2H), 7.69 (d, J=16.2 Hz, 1H).

Sources & evidence

ORD record
ord-dc2eed3d38714d09982f8562f3dc5f98
Source dataset
uspto-grants-2013_07
Patent number
US08487121B2

Reaction notes

Loading…