Triethylamine → HCID 44131782, compound

HRID 452278Notes

Reaction equation

HRID 452278 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.[CH:14]1([O:19][C:20]2[C:25]([O:26][CH3:27])=[CH:24][CH:23]=[CH:22][C:21]=2[CH2:28][CH2:29][CH2:30][C:31]([OH:33])=O)[CH2:18][CH2:17][CH2:16][CH2:15]1.CCN=C=NCCCN(C)C.[ClH:45].[CH:46]1[CH:47]=[CH:48][C:49]2N(O)N=N[C:50]=2[CH:51]=1.C(N(CC)CC)C>ClCCl>[Cl:45][C:46]1[CH:51]=[C:50]2[C:49](=[CH:48][CH:47]=1)[O:3][C:4]1([CH2:5][CH2:6][CH2:7]1)[CH2:9][CH:10]2[NH:12][C:31](=[O:33])[CH2:30][CH2:29][CH2:28][C:21]1[CH:22]=[CH:23][CH:24]=[C:25]([O:26][CH3:27])[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 68630863HCID 68630863, compound

Product 1

HCID 44131782HCID 44131782, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The title compound was prepared from Intermediate 2 (200 mg, 0.772 mmol) and 4-(2-cyclopentyloxy-3-methoxyphenyl)butanoic acid (214 mg, 0.772 mmol) in presence of EDCI.HCl (222 mg, 1.158 mmol), HOBt (118 mg, 0.772 mmol) and triethylamine (273 μl, 2.702 mmol) in dichloromethane (10 ml) as described in Example 1 to give 210 mg of the product as a white solid; IR (KBr) 3019, 2970, 1665, 1475, 1215, 769 cm−1; 1H NMR (300 MHz, CDCl3) δ 1.70-1.80 (m, 11H), 1.97-2.04 (m, 2H), 2.14-2.20 (m, 5H), 2.30-2.42 (m, 2H), 2.71 (t, J=6.9 Hz, 2H), 3.81 (s, 3H), 4.80 (br s, 1H), 5.24 (br s, 1H), 5.55 (d, J=8.7 Hz, 1H), 6.70-6.77 (m, 3H), 6.94 (t, J=7.2 Hz, 1H), 7.06 (d, J=9.9 Hz, 2H); ESI-MS (m/z) 482.44 (M−H)−.

Sources & evidence

ORD record
ord-3e2eaeac9faf4f4b90c7a8f66821ec9b
Source dataset
uspto-grants-2013_07
Patent number
US08487121B2

Reaction notes

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