Triethylamine → HCID 44131606, compound

HRID 452276Notes

Reaction equation

HRID 452276 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[C:22]2[C:21]3[CH:23]=[CH:24][CH:25]=[CH:26][C:20]=3[O:19][C:18]=2[C:17]([CH2:27][CH2:28][C:29]([OH:31])=O)=[CH:16][CH:15]=1.CCN=C=NCCCN(C)C.[ClH:43].[CH:44]1[CH:45]=[CH:46][C:47]2N(O)N=N[C:48]=2[CH:49]=1.C(N(CC)CC)C>ClCCl>[Cl:43][C:44]1[CH:49]=[C:48]2[C:47](=[CH:46][CH:45]=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:17]1[C:18]2[O:19][C:20]3[CH:26]=[CH:25][CH:24]=[CH:23][C:21]=3[C:22]=2[CH:14]=[CH:15][CH:16]=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 68791910HCID 68791910, compound

Product 1

HCID 44131606HCID 44131606, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The title compound was prepared from Intermediate 2 (200 mg, 0.896 mmol) and 3-dibenzo[b,d]furan-4-ylpropanoic acid (214 mg, 0.896 mmol) in presence of EDCI.HCl (256 mg, 1.345 mmol), HOBt (205 mg, 1.345 mmol) and triethylamine (371 μl, 2.690 mmol) in dichloromethane (10 ml) as described in Example 1 for 4 h to give 215 mg of the product as a white solid; 1H NMR (300 MHz, CDCl3) δ 1.81-1.91 (m, 3H), 2.08-2.13 (m, 3H), 2.17-2.26 (m, 2H), 2.72-2.79 (m, 2H), 3.35-3.41 (m, 2H), 5.16 (q, J=9.3 Hz, 1H), 5.44 (d, J=8.7 Hz, 1H), 6.63 (d, J=8.7 Hz, 1H), 6.82 (s, 1H), 6.99 (dd, J=6.3, 1.8 Hz, 1H), 7.28-7.33 (m, 3H), 7.42 (t, J=6.9 Hz, 1H), 7.53 (d, J=8.7 Hz, 1H), 7.82 (d, J=6.3 Hz, 1H), 7.91 (d, J=8.7 Hz, 1H); ESI-MS (m/z) 446.29 (M+H)+.

Sources & evidence

ORD record
ord-0c5e1d3df4344c4d932ba0273d31d7ac
Source dataset
uspto-grants-2013_07
Patent number
US08487121B2

Reaction notes

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