Triethylamine → HCID 44132760, compound

HRID 452263Notes

Reaction equation

HRID 452263 reaction equation
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.[CH:14]1([O:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=2[CH:26]([CH3:30])C(O)=O)[CH2:18][CH2:17][CH2:16][CH2:15]1.CCN=C=NCCCN(C)C.[ClH:42].C1C=CC2N([OH:52])N=NC=2C=1.C([N:55]([CH2:58][CH3:59])[CH2:56]C)C>ClCCl>[Cl:42][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)[CH2:59][CH:58]2[NH:55][C:56](=[O:52])[CH2:30][CH2:26][C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=1[O:19][CH:14]1[CH2:15][CH2:16][CH2:17][CH2:18]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 86648450HCID 86648450, compound

Product 1

HCID 44132760HCID 44132760, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The title compound was prepared from Intermediate 2 (200 mg, 0.779 mmol) and 3-[(2-cyclopentyloxyphenyl)propanoic acid (181 mg, 0.779 mmol) in presence of EDCI.HCl (222 mg, 1.152 mmol), HOBt (177 mg, 1.152 mmol) and triethylamine (427 μl, 3.116 mmol) in dichloromethane (10 ml) as described in Example 1 to give 150 mg of the product as a white solid; IR (KBr) 3316, 2952, 1651, 1488, 749 cm−1; 1H NMR (300 MHz, CDCl3) δ 1.58-1.65 (m, 3H), 1.72-1.87 (m, 8H), 2.02-2.12 (m, 3H), 2.26-2.36 (m, 2H), 2.56 (t, J=6.9 Hz, 2H), 2.95 (t, J=7.5 Hz, 2H), 4.72 (br s, 1H), 5.15 (q, J=8.7 Hz, 1H), 5.59 (d, J=7.8 Hz, 1H), 6.69 (d, J=8.4 Hz, 1H), 6.80-6.88 (m, 3H), 7.04 (dd, J=2.4, 5.7 Hz, 1H), 7.14 (d, J=7.5 Hz, 2H); ESI-MS (m/z) 440.34 (M)+.

Sources & evidence

ORD record
ord-0ab779a2d32d4ccca2b6d618c36355b3
Source dataset
uspto-grants-2013_07
Patent number
US08487121B2

Reaction notes

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