1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 117772579, compound

HRID 1478424Notes

Reaction equation

HRID 1478424 reaction equation
[CH2:1]([O:3][C@H:4]1[CH2:14][C@@H:13]([C:15]2[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=2)[O:12][C:6]2([CH2:11][CH2:10][NH:9][CH2:8][CH2:7]2)[CH2:5]1)[CH3:2].[F:22][C:23]1[CH:24]=[C:25]([CH:29]=[CH:30][C:31]=1[C:32]([OH:35])([CH3:34])[CH3:33])[C:26](O)=[O:27].CCN=C=NCCCN(C)C.C(N(C(C)C)CC)(C)C>C(Cl)Cl>[CH2:1]([O:3][C@H:4]1[CH2:14][C@@H:13]([C:15]2[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=2)[O:12][C:6]2([CH2:7][CH2:8][N:9]([C:26]([C:25]3[CH:29]=[CH:30][C:31]([C:32]([OH:35])([CH3:34])[CH3:33])=[C:23]([F:22])[CH:24]=3)=[O:27])[CH2:10][CH2:11]2)[CH2:5]1)[CH3:2]

Participants

6

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 81531DiisopropylethylamineHCID 682908483-Fluoro-4-(1-hydroxy-1-methyl-ethyl)benzoic acidHCID 117772408HCID 117772408, compound

Product 1

HCID 117772579HCID 117772579, compoundYield 23%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of cis-8-ethoxy-10-(4-fluorophenyl)-11-oxa-3-azaspiro[5.5]undecane (75 mg, 0.26 mmol) and 3-fluoro-4-(1-hydroxy-1-methyl-ethyl)benzoic acid (56 mg, 0.28 mmol) in CH2Cl2 (1 mL) was added EDCI (54 mg, 0.28 mmol). Diisopropylethylamine (134 μL, 0.767 mmol) was added last. The reaction mixture was allowed to stir at room temperature for 1 hour. The reaction mixture was purified by column chromatography (0-50% EtOAc-Hex) to provide [cis-8-ethoxy-10-(4-fluorophenyl)-11-oxa-3-azaspiro[5.5]undecan-3-yl]-[3-fluoro-4-(1-hydroxy-1-methyl-ethyl)phenyl]methanone (28.3 mg). 1H NMR (400 MHz, CDCl3) δ 7.60 (t, J=8.1 Hz, 1H), 7.34 (dd, J=8.5, 5.4 Hz, 2H), 7.14 (dd, J=8.0, 1.6 Hz, 1H), 7.11-7.00 (m, 3H), 4.60-4.30 (m, 2H), 3.77 (br s, 1H), 3.65-3.05 (m, 6H), 2.27 (br s, 2H), 2.23-2.07 (m, 1H), 1.64 (s, 6H), 1.62-1.30 (m, 5H), 1.22 (dd, J=16.6, 9.6 Hz, 3H). ESI-MS m/z calc. 473.24, found 474.5 (M+1)+; Retention time: 1.63 minutes (3 minute run).

Workup

  1. customThe reaction mixture was purified by column chromatography (0-50% EtOAc-Hex)

Sources & evidence

ORD record
ord-aa23fd9a144f4cee98e8d8c4c727b479
Source dataset
uspto-grants-2016_08
Patent number
US09403839B2

Reaction notes

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