1-Naphthaleneacetic Acid → HCID 44132437, compound

HRID 452256Notes

Reaction equation

HRID 452256 reaction equation
[C:1]12([CH2:13][CH:12]([NH2:14])[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[O:5]1)[CH2:4][CH2:3][CH2:2]2.[C:15]1([CH2:25][C:26]([OH:28])=O)[C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[CH:18]=[CH:17][CH:16]=1.CCN=C=NCCCN(C)C.[ClH:40].C1C=CC2N(O)N=NC=2C=1.C(N(CC)CC)C>ClCCl>[Cl:40][C:7]1[CH:8]=[CH:9][CH:10]=[C:11]2[C:6]=1[O:5][C:1]1([CH2:4][CH2:3][CH2:2]1)[CH2:13][C@H:12]2[NH:14][C:26](=[O:28])[CH2:25][C:15]1[C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[CH:18]=[CH:17][CH:16]=1

Participants

7

Reactant 5

HCID 68621-Naphthaleneacetic AcidHCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 59614620934554-38-8

Product 1

HCID 44132437HCID 44132437, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The title compound was prepared from Intermediate 3 (100 mg, 0.448 mmol) and 1-naphthylacetic acid (99 mg, 0.531 mmol) in presence of EDCI.HCl (128 mg, 0.672 mmol), HOBt (102 mg, 0.672 mmol) and triethylamine (185 μl, 2.022 mmol) in dichloromethane (10 ml) as described in Example 1 to give 100 mg of the product as a white solid; IR (KBr) 3271, 2938, 1636, 1449, 1244, 778 cm−1; 1H NMR (300 MHz, CDCl3) δ 1.62-1.78 (m, 5H), 2.11-2.30 (m, 3H), 4.09 (q, J=16.8 Hz, 2H), 5.23 (q, J=9.3 Hz, 1H), 5.46 (d, J=7.8 Hz, 1H), 6.52 (t, J=7.2 Hz, 1H), 6.60 (d, J=7.2 Hz, 1H), 7.07 (d, J=7.8 Hz, 1H), 7.37-7.42 (m, 2H), 7.48-7.59 (m, 2H), 7.77 (t, J=6.3 Hz, 1H), 7.84 (d, J=7.8 Hz, 1H), 7.99 (d, J=8.1 Hz, 1H); ESI-MS (m/z) 392.59 (M+H)+.

Sources & evidence

ORD record
ord-50675bfefae44e5d9edf51ed3a08cf88
Source dataset
uspto-grants-2013_07
Patent number
US08487121B2

Reaction notes

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