Triethylamine → HCID 44131947, compound

HRID 452279Notes

Reaction equation

HRID 452279 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.[CH:15]1([O:20][C:21]2[C:26]([O:27][CH3:28])=[CH:25][CH:24]=[CH:23][C:22]=2[CH2:29][CH2:30][CH2:31][C:32]([OH:34])=O)[CH2:19][CH2:18][CH2:17][CH2:16]1.CCN=C=NCCCN(C)C.[ClH:46].C1C=CC2N(O)N=NC=2C=1.C(N(CC)CC)C>ClCCl>[Cl:46][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:32](=[O:34])[CH2:31][CH2:30][CH2:29][C:22]1[CH:23]=[CH:24][CH:25]=[C:26]([O:27][CH3:28])[C:21]=1[O:20][CH:15]1[CH2:19][CH2:18][CH2:17][CH2:16]1

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 59614620934554-38-8HCID 68630863HCID 68630863, compound

Product 1

HCID 44131947HCID 44131947, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The title compound was prepared from Intermediate 3 (150 mg, 0.619 mmol) and 4-(2-cyclopentyloxy-3-methoxyphenyl)butanoic acid (205 mg, 0.739 mmol) in presence of EDCI.HCl (193 mg, 1.012 mmol), HOBt (154 mg, 1.012 mmol) and triethylamine (279 μl, 2.043 mmol) in dichloromethane (10 ml) as described in Example 1 to give 149 mg of the product as a white solid; IR (KBr) 3315, 2945, 1642, 1438, 1244, 1040 cm−1; 1H NMR (300 MHz, CDCl3) δ 1.57-1.70 (m, 10H), 1.97-2.04 (m, 4H), 2.14-2.20 (m, 4H), 2.40-2.47 (m, 2H), 2.66-2.72 (m, 2H), 3.80 (s, 3H), 4.79 (br s, 1H), 5.28 (d, J=6.3 Hz, 1H), 5.56 (d, J=8.4 Hz, 1H), 6.66-6.77 (m, 3H), 6.90-7.04 (m, 2H), 7.14-7.20 (m, 1H); ESI-MS (m/z) 484.26 (M)+.

Sources & evidence

ORD record
ord-75130045e75e47789ff6f99a9f7937f3
Source dataset
uspto-grants-2013_07
Patent number
US08487121B2

Reaction notes

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