Triethylamine → (2E)-2-(6-Chloro-3,4-dihydrospiro[chromene-2,1'-cyclobutan]-4-ylidene)-N-[2-(cyclopentyloxy)phenyl]acetamide

HRID 453932Notes

Reaction equation

HRID 453932 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:12](=[CH:13][CH:14]=1)[O:11][C:7]1([CH2:10][CH2:9][CH2:8]1)[CH2:6]/[C:5]/2=[CH:15]\[C:16](OCC)=[O:17].[CH:21]1([O:26][C:27]2[CH:33]=[CH:32][CH:31]=[CH:30][C:28]=2[NH2:29])[CH2:25][CH2:24][CH2:23][CH2:22]1.CCN=C=NCCCN(C)C.Cl.C1C=CC2N(O)N=NC=2C=1.C(N(CC)CC)C>ClCCl>[Cl:1][C:2]1[CH:3]=[C:4]2[C:12](=[CH:13][CH:14]=1)[O:11][C:7]1([CH2:10][CH2:9][CH2:8]1)[CH2:6]/[C:5]/2=[CH:15]\[C:16]([NH:29][C:28]1[CH:30]=[CH:31][CH:32]=[CH:33][C:27]=1[O:26][CH:21]1[CH2:25][CH2:24][CH2:23][CH2:22]1)=[O:17]

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 64853982-(Cyclopentyloxy)anilineHCID 86652760Ethyl (2E)-(6-chlorospiro[chromene-2,1'-cyclobutan]-4(3H)-ylidene)acetate2×

Product 1

HCID 58237898(2E)-2-(6-Chloro-3,4-dihydrospiro[chromene-2,1'-cyclobutan]-4-ylidene)-N-[2-(cyclopentyloxy)phenyl]acetamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The title compound was prepared by the coupling ethyl (2E)-(6-chlorospiro[chromene-2,1′-cyclobutan]-4(3H)-ylidene)acetate (Step 2 of Intermediate 1) with 2-(cyclopentyloxy)aniline (120 mg, 0.681 mmol) (150 mg, 0.565 mmol) in presence of EDCI.HCl (163 mg, 0.851 mmol), HOBt (130 mg, 0.851 mmol) and triethylamine (157 μl, 1.134 mmol) in dichloromethane (5 ml) as described in Method A to give 95 mg of the product as a white solid; 1H NMR (300 MHz, CDCl3) δ 1.53-1.65 (m, 8H), 1.74-1.90 (m, 4H), 2.22-2.30 (m, 2H), 2.47-2.57 (m, 2H), 3.50 (s, 2H), 4.67 (br s, 1H), 6.75 (d, J=8.1 Hz, 2H), 6.85-6.96 (m, 2H), 7.04-7.10 (m, 2H), 8.32 (d, J=7.8 Hz, 1H).

Sources & evidence

ORD record
ord-64794c33638a4227b6dc18afbc65b0bd
Source dataset
uspto-grants-2013_07
Patent number
US08492568B2

Reaction notes

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