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

HRID 452252Notes

Reaction equation

HRID 452252 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([O:19][C:20]2[C:25]([O:26][CH3:27])=[CH:24][CH:23]=[CH:22][C:21]=2[CH2:28][C:29]([OH:31])=O)[CH2:18][CH2:17][CH2:16][CH2:15]1.CCN=C=NCCCN(C)C.[ClH:43].[CH:44]1[CH:45]=[CH:46][C:47]2N(O)N=N[C:48]=2[CH:49]=1.C(N(CC)CC)C>ClCCl>[Cl:43][C:44]1[CH:49]=[C:48]2[C:47](=[CH:46][CH:45]=1)[O:3][C:4]1([CH2:5][CH2:6][CH2:7]1)[CH2:9][CH:10]2[NH:12][C:29](=[O:31])[CH2:28][C:21]1[CH:22]=[CH:23][CH:24]=[C:25]([O:26][CH3:27])[C:20]=1[O:19][CH:14]1[CH2:15][CH2:16][CH2:17][CH2:18]1

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 153387052,2-dimethyl-3,4-dihydro-2H-1-benzopyran-4-amineHCID 68628470[2-(Cyclopentyloxy)-3-methoxyphenyl]acetic acid

Product 1

HCID 44132274N-(6-Chloro-3,4-dihydrospiro[chromene-2,1'-cyclobutan]-4-yl)-2-(2-(cyclopentyloxy)-3-methoxyphenyl)acetamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The title compound was prepared from Intermediate 2 (200 mg, 0.763 mmol) in dichloromethane (10 ml) and [2-(cyclopentyloxy)-3-methoxyphenyl]acetic acid (283 mg, 1.153 mmol) in presence of EDCI.HCl (221 mg, 1.153 mmol), HOBt (178 mg, 1.153 mmol) and triethylamine (321 μl, 2.307 mmol) as described in Example 1 to give 236 mg of the product as a white solid; IR (KBr) 3311, 2963, 1653, 1529, 1476, 1266, 813 cm−1; 1H NMR (300 MHz, CDCl3) δ 1.58-1.64 (m, 6H), 1.70-1.80 (m, 6H), 1.97-2.04 (m, 1H), 2.13 (t, J=7.8 Hz, 2H), 2.26-2.33 (m, 2H), 3.58 (q, J=14.4 Hz, 2H), 3.81 (s, 3H), 4.99 (br s, 1H), 5.09-5.17 (m, 1H), 6.31 (d, J=8.1 Hz, 1H), 6.66 (t, J=8.4 Hz, 1H), 6.81-7.02 (m, 4H).

Sources & evidence

ORD record
ord-0f73b48417a140179b2a199f47779261
Source dataset
uspto-grants-2013_07
Patent number
US08487121B2

Reaction notes

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