Ethyl chloroformate → HCID 57993248, compound

HRID 508625Notes

Reaction equation

HRID 508625 reaction equation
[NH2:1][C:2]1([CH2:7][N:8]2[CH2:13][CH2:12][CH:11]([CH2:14][NH:15][C:16](=[O:31])[C:17]3[CH:22]=[C:21]([C:23]([F:26])([F:25])[F:24])[CH:20]=[C:19]([C:27]([F:30])([F:29])[F:28])[CH:18]=3)[CH2:10][CH2:9]2)[CH2:6][CH2:5][CH2:4][CH2:3]1.CCN(C(C)C)C(C)C.Cl[C:42]([O:44][CH2:45][CH3:46])=[O:43]>C(Cl)Cl.C(OCC)(=O)C>[F:30][C:27]([F:28])([F:29])[C:19]1[CH:18]=[C:17]([CH:22]=[C:21]([C:23]([F:24])([F:25])[F:26])[CH:20]=1)[C:16]([NH:15][CH2:14][CH:11]1[CH2:12][CH2:13][N:8]([CH2:7][C:2]2([NH:1][C:42](=[O:43])[O:44][CH2:45][CH3:46])[CH2:6][CH2:5][CH2:4][CH2:3]2)[CH2:9][CH2:10]1)=[O:31]

Participants

6

Reactant 3

HCID 10928Ethyl chloroformateHCID 81531DiisopropylethylamineHCID 57993626HCID 57993626, compound

Product 1

HCID 57993248HCID 57993248, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of N-((1-((1-aminocyclopentyl)methyl)piperidin-4-yl)methyl)-3,5-bis(trifluoromethyl)benzamide (100 mg, 0.28 mmol) and i-Pr2NEt (0.2 mL, 1.1 mmol) in CH2Cl2 (5 mL) was added ethyl chloroformate (0.05 mL, 0.53 mmol). The reaction mixture was allowed to stir at room temperature for 18 hours and then diluted with ethyl acetate. The organic fraction was washed with sat. NaHCO3, and then brine and dried over Na2SO4. The solvent was removed and the crude was purified by HiTOPs to provide ethyl 1-((4-((3,5-bis(trifluoromethyl)benzamido)methyl)piperidin-1-yl)methyl)cyclopentylcarbamate.

Workup

  1. washThe organic fraction was washed with sat. NaHCO3
  2. dry with materialbrine and dried over Na2SO4
  3. customThe solvent was removed
  4. customthe crude was purified by HiTOPs

Sources & evidence

ORD record
ord-7c5c839e473d45db965863d8ccf90597
Source dataset
uspto-grants-2015_08
Patent number
US09096522B2

Reaction notes

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