Triethylamine → HCID 44132599, compound

HRID 452259Notes

Reaction equation

HRID 452259 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.[CH2:14]1[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH2:17][CH2:16][CH:15]1[CH2:24][C:25]([OH:27])=O.CCN=C=NCCCN(C)C.[ClH:39].[CH:40]1[CH:41]=[CH:42][C:43]2N(O)N=N[C:44]=2[CH:45]=1.C(N(CC)CC)C>ClCCl>[Cl:39][C:40]1[CH:45]=[C:44]2[C:43](=[CH:42][CH:41]=1)[O:3][C:4]1([CH2:5][CH2:6][CH2:7]1)[CH2:9][CH:10]2[NH:12][C:25](=[O:27])[CH2:24][CH:15]1[CH2:16][CH2:17][C:18]2[C:23](=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH2:14]1

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 100127392-(1,2,3,4-tetrahydronaphthalen-2-yl)acetic acidHCID 153387052,2-dimethyl-3,4-dihydro-2H-1-benzopyran-4-amine

Product 1

HCID 44132599HCID 44132599, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The title compound was prepared from Intermediate 2 (218 mg, 1.053 mmol) and 1,2,3,4-tetrahydronaphthalen-2-ylacetic acid (200 mg, 1.053 mmol) in presence of EDCI.HCl (302 mg, 1.585 mmol), HOBt (241 mg, 1.585 mmol) and triethylamine (439 μl, 3.165 mmol) in dichloromethane (10 ml) as described in Example 1 to give 40 mg of the product as a white solid; IR (KBr) 3250, 2931, 2343, 1635, 1474, 1232, 738 cm−1; 1H NMR (300 MHz, CDCl3) δ 1.67-1.82 (m, 3H), 1.83-1.95 (m, 2H), 2.21-2.29 (m, 3H), 2.30-2.39 (m, 4H), 2.48-2.59 (m, 1H), 2.85-2.96 (m, 3H), 5.32 (q, J=7.8 Hz, 1H), 5.59 (d, J=7.8 Hz, 1H), 6.73 (d, J=8.4 Hz, 1H), 6.73 (d, J=8.4 Hz, 1H), 7.08-7.14 (m, 6H); ESI-MS (m/z) 396.95 (M+H)+.

Sources & evidence

ORD record
ord-a9f41701ea1940f2aca1922256663164
Source dataset
uspto-grants-2013_07
Patent number
US08487121B2

Reaction notes

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