Triethylamine → HCID 44134164, compound

HRID 452272Notes

Reaction equation

HRID 452272 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.[CH3:14][C:15]1[O:16][C:17]2[C:23]([O:24][CH3:25])=[CH:22][CH:21]=[C:20]([CH2:26][CH2:27][C:28]([OH:30])=O)[C:18]=2[CH:19]=1.CCN=C=NCCCN(C)C.[ClH:42].[CH:43]1[CH:44]=[CH:45][C:46]2N(O)N=N[C:47]=2[CH:48]=1.C(N(CC)CC)C>ClCCl>[Cl:42][C:43]1[CH:48]=[C:47]2[C:46](=[CH:45][CH:44]=1)[O:3][C:4]1([CH2:5][CH2:6][CH2:7]1)[CH2:9][CH:10]2[NH:12][C:28](=[O:30])[CH2:27][CH2:26][C:20]1[C:18]2[CH:19]=[C:15]([CH3:14])[O:16][C:17]=2[C:23]([O:24][CH3:25])=[CH:22][CH:21]=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 68629882HCID 68629882, compound

Product 1

HCID 44134164HCID 44134164, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The title compound was prepared from Intermediate 2 (200 mg, 0.896 mmol) and 3-(2-methyl, 7-methoxy-1-benzofuran-4-yl)propanoic acid (209 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 for 4 h to give 60 mg of the product as a white solid; IR (KBr) 3395, 2972, 1642, 1515, 1423, 1235, 775 cm−1; 1H NMR (300 MHz, CDCl3) δ 1.41-1.61 (m, 4H), 1.90-1.98 (m, 4H), 2.46 (s, 3H), 2.55-2.62 (m, 2H), 3.96 (s, 3H), 5.10-5.16 (m, 1H), 5.26 (d, J=8.4 Hz, 2H), 6.40-6.46 (m, 1H), 6.60-6.70 (m, 3H), 6.83 (s, 1H), 6.91 (d, J=7.8 Hz, 1H), 7.02 (d, J=7.5 Hz, 1H); ESI-MS (m/z) 395.63 (M+H)+.

Sources & evidence

ORD record
ord-c4d62f6d07d3430da7f3a74904a6042a
Source dataset
uspto-grants-2013_07
Patent number
US08487121B2

Reaction notes

Loading…