Ethyl chloroformate → HCID 57993248, compound

HRID 388765Notes

Reaction equation

HRID 388765 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-2407a5bfcbbf44b6bbc344c009a926b0
Source dataset
uspto-grants-2013_02
Patent number
US08377968B2

Reaction notes

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