Triethylamine → HCID 44133984, compound

HRID 452269Notes

Reaction equation

HRID 452269 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:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH:17]=[CH:16][C:15]=1[CH2:24][CH2:25][C:26]([OH:28])=O.CCN=C=NCCCN(C)C.[ClH:40].[CH:41]1[CH:42]=[CH:43][C:44]2N(O)N=N[C:45]=2[CH:46]=1.C(N(CC)CC)C>ClCCl>[Cl:40][C:41]1[CH:46]=[C:45]2[C:44](=[CH:43][CH:42]=1)[O:3][C:4]1([CH2:5][CH2:6][CH2:7]1)[CH2:9][CH:10]2[NH:12][C:26](=[O:28])[CH2:25][CH2:24][C:15]1[CH:16]=[CH:17][C:18]2[C:23](=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH:14]=1

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 2386763-(naphthalen-2-yl)propanoic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 153387052,2-dimethyl-3,4-dihydro-2H-1-benzopyran-4-amine

Product 1

HCID 44133984HCID 44133984, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The title compound was prepared from Intermediate 2 (100 mg, 0.506 mmol) and 3-(2-naphthyl)propanoic acid (103 mg, 0.506 mmol) in presence of EDCI.HCl (143 mg, 0.751 mmol), HOBt (114 mg, 0.751 mmol) and triethylamine (209 μl, 1.518 mmol) in dichloromethane (10 ml) as described in Example 1 for 3 h to give 101 mg of the product as a white solid; IR (KBr) 3287, 2937, 1645, 1475, 1234, 817 cm−1; 1H NMR (300 MHz, CDCl3) δ 1.41-1.48 (m, 1H), 1.80-1.86 (m, 2H), 2.06-2.26 (m, 4H), 2.56-2.68 (m, 2H), 3.19 (t, J=7.2 Hz, 2H), 3.47 (s, 1H), 5.17 (q, J=9.0 Hz, 1H), 5.35 (d, J=7.8 Hz, 1H), 6.65 (d, J=8.7 Hz, 1H), 6.91 (s, 1H), 7.01 (d, J=8.4 Hz, 1H), 7.33-7.42 (m, 3H), 7.65 (s, 1H), 7.77 (d, J=8.1 Hz, 3H); ESI-MS (m/z) 406.56 (M+H)+.

Sources & evidence

ORD record
ord-da945cd6784e45c3bc0080f408e508b6
Source dataset
uspto-grants-2013_07
Patent number
US08487121B2

Reaction notes

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