Triethylamine → N-(6-Chloro-3,4-dihydrospiro[chromene-2,1'-cyclobutan]-4-yl)-3-(1-naphthyl)-propanamide

HRID 452268Notes

Reaction equation

HRID 452268 reaction equation
C[C:2]1([CH3:13])[CH2:11][CH:10](N)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[O:3]1.[C:14]1([CH:24]([CH3:28])C(O)=O)[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH:17]=[CH:16][CH:15]=1.CCN=C=NCCCN(C)C.[ClH:40].C1C=CC2N([OH:50])N=NC=2C=1.C([N:53]([CH2:56][CH3:57])[CH2:54]C)C>ClCCl>[Cl:40][C:7]1[CH:8]=[C:9]2[C:4](=[CH:5][CH:6]=1)[O:3][C:2]1([CH2:11][CH2:10][CH2:13]1)[CH2:57][CH:56]2[NH:53][C:54](=[O:50])[CH2:28][CH2:24][C:14]1[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH:17]=[CH:16][CH:15]=1

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 1227522-(Naphthalen-1-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 44133803N-(6-Chloro-3,4-dihydrospiro[chromene-2,1'-cyclobutan]-4-yl)-3-(1-naphthyl)-propanamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The title compound was prepared from Intermediate 2 (200 mg, 0.896 mmol) and 1-naphthylpropanoic acid (178 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 to give 160 mg of the product as a white solid; 1H NMR (300 MHz, CDCl3) δ 1.43-1.51 (m, 1H), 1.63-1.69 (m, 1H), 1.81-1.97 (m, 2H), 2.09-2.26 (m, 4H), 2.64-2.70 (m, 2H), 3.50 (t, J=7.2 Hz, 2H), 5.14 (q, J=9.9 Hz, 1H), 5.26 (d, J=8.4 Hz, 1H), 6.65 (d, J=8.7 Hz, 1H), 6.82 (s, 1H), 7.01 (dd, J=2.4, 8.7 Hz, 1H), 7.35-7.54 (m, 4H), 7.73 (d, J=6.9 Hz, 1H), 7.84 (d, J=7.5 Hz, 1H), 8.04 (d, J=8.1 Hz, 1H); ESI-MS (m/z) 406.34 (M+H)+.

Sources & evidence

ORD record
ord-ca1ed5624ea0447bbed871dbcd618669
Source dataset
uspto-grants-2013_07
Patent number
US08487121B2

Reaction notes

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