Triethylamine → HCID 44132113, compound

HRID 452280Notes

Reaction equation

HRID 452280 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][O:15][C:16]1[C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[C:19]([C:26](=[O:32])[CH2:27][CH2:28][C:29]([OH:31])=O)=[CH:18][CH:17]=1.CCN=C=NCCCN(C)C.[ClH:44].[CH:45]1[CH:46]=[CH:47][C:48]2N(O)N=N[C:49]=2[CH:50]=1.C(N(CC)CC)C>ClCCl>[Cl:44][C:45]1[CH:50]=[C:49]2[C:48](=[CH:47][CH:46]=1)[O:3][C:4]1([CH2:5][CH2:6][CH2:7]1)[CH2:9][CH:10]2[NH:12][C:29](=[O:31])[CH2:28][CH2:27][C:26](=[O:32])[C:19]1[C:20]2[C:25](=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:16]([O:15][CH3:14])=[CH:17][CH:18]=1

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 71818MenbutoneHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 153387052,2-dimethyl-3,4-dihydro-2H-1-benzopyran-4-amine

Product 1

HCID 44132113HCID 44132113, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The title compound was prepared from Intermediate 2 (250 mg, 0.965 mmol) and 4-(4-methoxy-1-naphthyl)-4-oxobutanoic acid (274 mg, 1.062 mmol) in presence of EDCI.HCl (277 mg, 1.451 mmol), HOBt (221 mg, 1.459 mmol) and triethylamine (403 μl, 2.905 mmol) in dichloromethane (10 ml) as described in Example 1 to give 311 mg of the product as a white solid; IR (KBr) 3204, 2972, 1632, 1523, 1230, 757 cm−1; 1H NMR (300 MHz, CDCl3) δ 1.67-1.73 (m, 2H), 2.06-2.31 (m, 6H), 2.66-2.71 (m, 2H), 3.31-3.39 (m, 2H), 4.05 (s, 3H), 5.05 (br s, 1H), 6.77 (d, J=9.0 Hz, 1H), 7.03 (d, J=8.4 Hz, 1H), 7.14 (d, J=8.4 Hz, 1H), 7.20 (s, 1H), 7.53-7.61 (m, 2H), 8.20-8.28 (m, 2H), 8.43 (d, J=8.4 Hz, 1H), 8.86 (d, J=8.7 Hz, 1H); ESI-MS (m/z) 464.17 (M+H)+.

Sources & evidence

ORD record
ord-4ed6c398a2284c95bd8a941165ed4abd
Source dataset
uspto-grants-2013_07
Patent number
US08487121B2

Reaction notes

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