Triethylamine → HCID 68793904, compound

HRID 452265Notes

Reaction equation

HRID 452265 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.[N:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1/[CH:26]=[CH:27]/[C:28]([OH:30])=O.CCN=C=NCCCN(C)C.[ClH:42].[CH:43]1[CH:44]=[CH:45][C:46]2N(O)N=N[C:47]=2[CH:48]=1.C(N(CC)CC)C>ClCCl>[Cl:42][C:43]1[CH:48]=[C:47]2[C:46](=[CH:45][CH:44]=1)[O:3][C:4]1([CH2:5][CH2:6][CH2:7]1)[CH2:9][CH:10]2[NH:12][C:28](=[O:30])/[CH:27]=[CH:26]/[C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=1[C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][N:14]=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 68790670(2E)-3-[2-(2-Pyridinyl)phenyl]-2-propenoic acid

Product 1

HCID 68793904HCID 68793904, compoundYield 80.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

This compound was prepared from Intermediate 2 (300 mg, 1.153 mmol) and (2E)-3-(2-pyridin-2-ylphenyl)acrylic acid (260 mg, 1.153 mmol) in presence of EDCI.HCl (332 mg, 1.730 mmol), HOBt (177 mg, 1.153 mmol) and triethylamine (402 μl, 2.884 mmol) in dichloromethane (10 ml) as described in Example 1 to give 400 mg of the product as a white solid; IR (Neat) 3228, 2935, 1651, 1540, 1475, 1264, 759 cm−1; 1H NMR (300 MHz, CDCl3) δ 1.80-1.90 (m, 2H), 2.08-2.20 (m, 4H), 2.35-2.49 (m, 2H), 3.46 (q, J=7.2 Hz, 1H), 5.34 (q, J=9.3 Hz, 1H), 5.84 (d, J=8.7 Hz, 1H), 6.37 (d, J=15.0 Hz, 1H), 6.73 (d, J=8.1 Hz, 1H), 7.08 (d, J=8.4 Hz, 1H), 7.14 (s, 1H), 7.33-7.43 (m, 4H), 7.61-7.70 (m, 3H), 8.55-8.61 (m, 2H); ESI-MS (m/z) 431.24 (M+H)+.

Sources & evidence

ORD record
ord-d8fb1e057ebd4d83a58a67514898cdfb
Source dataset
uspto-grants-2013_07
Patent number
US08487121B2

Reaction notes

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