Triethylamine → HCID 44132439, compound

HRID 452257Notes

Reaction equation

HRID 452257 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][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][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 113932-Naphthaleneacetic acidHCID 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 44132439HCID 44132439, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The title compound was prepared from Intermediate 2 (200 mg, 0.764 mmol) and 2-naphthylacetic acid (213 mg, 1.141 mmol) in presence of EDCI.HCl (213 mg, 1.145 mmol), HOBt (176 mg, 1.145 mmol) and triethylamine (425 μl, 3.052 mmol) in dichloromethane (10 ml) as described in Example 1 to give 193 mg of the product as a white solid; IR (KBr) 3262, 2933, 1643, 1474, 1230, 816 cm−1; 1H NMR (300 MHz, CDCl3) δ 1.63-1.77 (m, 2H), 1.84-1.92 (m, 2H), 1.95-2.02 (m, 2H), 2.16-2.36 (m, 2H), 3.82 (s, 2H), 5.24 (q, J=9.6 Hz, 1H), 5.50 (d, J=8.7 Hz, 1H), 6.65 (d, J=8.4 Hz, 1H), 7.00 (d, J=9.3 Hz, 2H), 7.39 (d, J=8.4 Hz, 1H), 7.45-7.50 (m, 2H), 7.73 (s, 1H), 7.78-7.86 (m, 3H); ESI-MS (m/z) 392.58 (M+H)+.

Sources & evidence

ORD record
ord-76bc6c61aca54dfda3369140a142fcd5
Source dataset
uspto-grants-2013_07
Patent number
US08487121B2

Reaction notes

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