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

HRID 452250Notes

Reaction equation

HRID 452250 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.[N+:14]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[CH2:23][C:24]([OH:26])=O)([O-:16])=[O:15].CCN=C=NCCCN(C)C.[ClH:38].[CH:39]1[CH:40]=[CH:41][C:42]2N(O)N=N[C:43]=2[CH:44]=1.C(N(CC)CC)C>ClCCl>[Cl:38][C:39]1[CH:44]=[C:43]2[C:42](=[CH:41][CH:40]=1)[O:3][C:4]1([CH2:5][CH2:6][CH2:7]1)[CH2:9][CH:10]2[NH:12][C:24](=[O:26])[CH2:23][C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=1[N+:14]([O-:16])=[O:15]

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 77337(2-Nitrophenyl)acetic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 153387052,2-dimethyl-3,4-dihydro-2H-1-benzopyran-4-amine

Product 1

HCID 68794524N-(6-chloro-3,4-dihydrospiro[chromene-2,1'-cyclobutan]-4-yl)-2-(2-nitrophenyl)acetamideYield 79.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

This compound was prepared from Intermediate 2 (500 mg, 1.923 mmol) and 2-nitrophenylacetic acid (348 mg, 1.923 mmol) in presence of EDCI.HCl (191 mg, 1.789 mmol), HOBt (153 mg, 1.789 mmol) and triethylamine (802 μl, 2.289 mmol) in dichloromethane (10 ml) as described in Example 1 for 6 h to give 550 mg of the product as a white solid. 1H NMR (300 MHz, CDCl3) δ 1.67-1.84 (m, 5H), 2.10-2.18 (m, 2H), 2.32-2.43 (m, 2H), 3.91 (s, 2H), 5.19-5.27 (m, 1H), 5.92-5.98 (m, 1H), 6.71 (d, J=9.3 Hz, 1H), 7.00-7.08 (m, 1H), 7.45-7.53 (m, 2H), 7.64 (d, J=7.5 Hz, 1H), 8.05 (d, J=8.9 Hz, 1H).

Sources & evidence

ORD record
ord-d89178d1a5244faf867d95b5792f3d21
Source dataset
uspto-grants-2013_07
Patent number
US08487121B2

Reaction notes

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