Tetrahydrofuran → HCID 58920191, compound

HRID 1365519Notes

Reaction equation

HRID 1365519 reaction equation
[CH:1]1([NH:6][C:7]([NH:9][C:10]([C:29]2[CH:34]=[CH:33][C:32]([N:35]=C(C3C=CC=CC=3)C3C=CC=CC=3)=[CH:31][N:30]=2)([C:18]2[CH:23]=[C:22]([C:24]([F:27])([F:26])[F:25])[CH:21]=[C:20]([F:28])[CH:19]=2)[CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[O:8])[CH2:5][CH2:4][CH2:3][CH2:2]1.C1COCC1.CCOC(C)=O>Cl>[NH2:35][C:32]1[CH:33]=[CH:34][C:29]([C:10]([NH:9][C:7]([NH:6][CH:1]2[CH2:5][CH2:4][CH2:3][CH2:2]2)=[O:8])([C:18]2[CH:23]=[C:22]([C:24]([F:26])([F:27])[F:25])[CH:21]=[C:20]([F:28])[CH:19]=2)[CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[N:30][CH:31]=1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 8857Ethyl AcetateHCID 58921245HCID 58921245, compound

Product 1

HCID 58920191HCID 58920191, compoundYield 90.3%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

1-Cyclopentyl-3-(1-(5-(diphenylmethyleneamino)pyridin-2-yl)-1-(3-fluoro-5-(trifluoromethyl)phenyl)-2-phenylethyl)urea (77 mg, 0. 12 mmol) was stirred in 2N HCl (1.5 mL) and THF (6 mL) at room temperature for 30 min. LC-MS showed completion of the reaction. EtOAc was added and the solution was washed with saturated NaHCO3, H2O, brine, dried (Na2SO4), filtered, and concentrated to dryness. The residue was purified by flash chromatography (silica gel, hexanes/EtOAc, came out 45-50% EtOAc in hexanes) to give 1-(1-(5-aminopyridin-2-yl)-1-(3-fluoro-5-(trifluoromethyl)phenyl)-2-phenylethyl)-3-cyclopentylurea as colorless film (52 mg, yield: 90.3%). LC-MS ESI 487.32 (M+H) (10-90% MeOH in H2O with 0.1% TFA in a 4-min run, retention time=3.29 min). 1H NMR (400 MHz, CDCl3) δ ppm 1.23-1.32 (m, 1 H), 1.39-1.50 (m, 1 H), 1.58-1.69 (m, 4 H), 1.86 (dt, J=12.47, 6.24 Hz, 1 H), 1.99-2.08 (m, 1 H), 3.54 (d, J=12.47 Hz, 1 H), 3.74 (s, br, 1 H), 3.89-4.00 (m, 1 H), 4.33 (d, J=7.09 Hz, 1 H), 4.44 (d, J=12.47 Hz, 1H), 6.65-6.72 (m, 2 H), 6.88-6.93 (m, 1 H), 6.97-7.02 (m, 1 H), 7.07-7.19 (m, 4 H), 7.22-7.31 (m, 1 H), 7.39 (d, J=10.03 Hz, 1 H), 7.55 (s, 1 H), 7.75 (d, J=2.69 Hz, 1H).

Workup

  1. customcompletion of the reaction
  2. washthe solution was washed with saturated NaHCO3, H2O, brine
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated to dryness
  6. customThe residue was purified by flash chromatography (silica gel, hexanes/EtOAc

Sources & evidence

ORD record
ord-2f774d73fa4442fcbad829533c791ebc
Source dataset
uspto-grants-2011_02
Patent number
US07888376B2

Reaction notes

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