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

HRID 452258Notes

Reaction equation

HRID 452258 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.[C:14]1([CH2:24][C:25]([OH:27])=O)[C:23]2[CH2:22][CH2:21][CH2:20][CH2:19][C:18]=2[CH:17]=[CH:16][CH:15]=1.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][CH:14]1[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH2:17][CH2:16][CH2:15]1

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 2319782-(5,6,7,8-Tetrahydronaphthalen-1-yl)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 44132598N-(6-Chloro-3,4-dihydrospiro[chromene-2,1'-cyclobutan]-4-yl)-2-(1,2,3,4-tetrahydro naphthalen-1-yl)acetamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The title compound was prepared from Intermediate 2 (212 mg, 0.951 mmol) and 5,6,7,8-tetrahydronaphthalen-1-ylacetic acid (150 mg, 0.791 mmol) in presence of EDCI.HCl (227 mg, 1.663 mmol), HOBt (121 mg, 0.791 mmol) and triethylamine (330 μl, 2.371 mmol) in dichloromethane (10 ml) as described in Example 1 to give 154 mg of the product as a white solid; IR (KBr) 3278, 2935, 1637, 1474, 1263, 818 cm−1; 1H NMR (300 MHz, CDCl3) δ 1.70-1.87 (m, 6H), 2.03-2.18 (m, 3H), 2.20-2.46 (m, 3H), 2.60-2.70 (m, 1H), 2.77 (br s, 2H), 3.47 (br s, 2H), 5.27 (q, J=9.3 Hz, 1H), 5.45 (d, J=7.8 Hz, 1H), 6.70 (d, J=8.7 Hz, 1H), 7.05-7.18 (m, 6H); ESI-MS (m/z) 394.76 (M−H)−.

Sources & evidence

ORD record
ord-56d7ff260f8240d5a3e29572de0b2d45
Source dataset
uspto-grants-2013_07
Patent number
US08487121B2

Reaction notes

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