Butylamine → HCID 86691026, compound

HRID 1191958Notes

Reaction equation

HRID 1191958 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([F:26])[S:12][C:11]([C:13]3[CH:23]=[CH:22][C:16]([O:17][CH2:18][C:19](O)=[O:20])=[CH:15][CH:14]=3)=[N:10][C:9]2([F:25])[F:24])=[CH:4][CH:3]=1.C1[CH:28]=[CH:29][C:30]2N(O)N=[N:33][C:31]=2C=1.CCN=C=NCCCN(C)C.Cl.C(N)CCC>CN(C=O)C.ClCCl>[CH2:31]([NH:33][C:19](=[O:20])[CH2:18][O:17][C:16]1[CH:22]=[CH:23][C:13]([C:11]2[S:12][C:8]([C:5]3[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=3)([F:26])[C:9]([F:24])([F:25])[N:10]=2)=[CH:14][CH:15]=1)[CH2:30][CH2:29][CH3:28]

Participants

7

Reactant 4

HCID 8007ButylamineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 86691027HCID 86691027, compound

Product 1

HCID 86691026HCID 86691026, compoundYield 35%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-(4-(5-(4-chlorophenyl)-4,4,5-trifluoro-4,5-dihydrothiazol-2-yl)phenoxy)acetic acid (45.7 mg, 114 μmol) in DMF (5.7 mL) were added the coupling agents HOBt (18.4 mg, 136 μmol) and EDC.HCl (26.1 mg, 0.136 mmol). Then, butylamine was added (13.6 μL, 136 μmol) and the mixture was stirred for 2 h at room temperature. When the reaction was completed, it was diluted with dicloromethane (20 mL) and washed with H2O (3×5 mL). The organic extracts were dried over Na2SO4, filtered and evaporated under reduced pressure. The residue was absorbed onto silica then subjected to flash chromatography (SiO2, hexane:AcOEt, 6:4), obtaining 18.1 mg of N-butyl-2-(4-(5-(4-chlorophenyl)-4,4,5-trifluoro-4,5-dihydrothiazol-2-yl)phenoxy)acetamide (35% yield). RMN1H (CDCl3, 400 MHz): δ 8.03-7.93; (m, 2H), 7.64; (d, J=8.3 Hz, 2H), 7.45; (d, J=8.4 Hz, 2H), 7.09-7.01; (m, 2H), 6.48; (bs, 1H), 4.58; (s,), 3.53-3.26; (m, 2H), 1.59-1.50; (m, 2H), 1.41-1.34; (m, 2H), 0.98-0.90; (m, 3H) ppm. RMN19F (CDCl3, 400 MHz): δ −78.81; (dd, J=217.4, 9.8 Hz), −103.30; (dd, J=217.3, 8.8 Hz), −130.96; (m, J=9.3 Hz) ppm.

Workup

  1. washwashed with H2O (3×5 mL)
  2. dry with materialThe organic extracts were dried over Na2SO4
  3. filtrationfiltered
  4. customevaporated under reduced pressure
  5. customThe residue was absorbed onto silica

Sources & evidence

ORD record
ord-1d3f9f4d2c07494cbfd81805f91e7497
Source dataset
uspto-grants-2014_03
Patent number
US08680126B2

Reaction notes

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