Cyclohexanecarbonyl chloride → HCID 86645373, compound

HRID 1972287Notes

Reaction equation

HRID 1972287 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C@@H:12]([C:13]3[CH:18]=[CH:17][CH:16]=[C:15]([C:19]([F:22])([F:21])[F:20])[CH:14]=3)[CH2:11][N:10]([CH2:23][CH2:24][C:25](=[N:27][OH:28])[NH2:26])[C:9]2=[O:29])=[CH:4][CH:3]=1.[CH:30]1([C:36](Cl)=[O:37])[CH2:35][CH2:34][CH2:33][CH2:32][CH2:31]1.C(N(C(C)C)CC)(C)C>ClCCl.C(OCC)(=O)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C@@H:12]([C:13]3[CH:18]=[CH:17][CH:16]=[C:15]([C:19]([F:22])([F:21])[F:20])[CH:14]=3)[CH2:11][N:10]([CH2:23][CH2:24][C:25](=[N:27][O:28][C:36]([CH:30]3[CH2:35][CH2:34][CH2:33][CH2:32][CH2:31]3)=[O:37])[NH2:26])[C:9]2=[O:29])=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 75938Cyclohexanecarbonyl chlorideHCID 81531DiisopropylethylamineHCID 86645372HCID 86645372, compound

Product 1

HCID 86645373HCID 86645373, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

(S)-3-(3-(4-chlorophenyl)-2-oxo-4-(3-(trifluoromethyl)phenyl)-imidazolidin-1-yl)-N′-hydroxypropanimidamide (28.7 mg, 0.067 mmol) is dissolved in dichloromethane (2 mL). Cyclohexanecarbonyl chloride (14.8 mg, 0.10 mmol) and diisopropyl ethylamine (26.3 mg, 0.20 mmol) are then added. The reaction is stirred for 3 h at room temperature. The reaction is diluted with ethyl acetate followed by quenching with sat. sodium bicarbonate solution. The organic layer is washed with brine and dried with MgSO4. The solvents is removed under vacuum to afford crude (S)-3-(3-(4-chlorophenyl)-2-oxo-4-(3-(trifluoromethyl)phenyl)imidazolidin-1-yl)-N′-(cyclohexanecarbonyloxy)propanimidamide which is used directly in the next step without further purification. HPLC-MS calculated for C26H29ClF3N4O3 (M+H+) 537.1, found 537.1.

Workup

  1. customby quenching with sat. sodium bicarbonate solution
  2. washThe organic layer is washed with brine
  3. dry with materialdried with MgSO4
  4. customThe solvents is removed under vacuum

Sources & evidence

ORD record
ord-e3346f16a76745fca32004d87117bb01
Source dataset
uspto-grants-2013_04
Patent number
US08431607B2

Reaction notes

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