Hydrochloric Acid → 5-Fluoro-1-[(2-oxopiperazin-1-yl)methyl]-2,3-dihydro-1H-indene-4-carbonitrile

HRID 1466077Notes

Reaction equation

HRID 1466077 reaction equation
C(OC([N:8]([CH2:18][CH:19]1[C:27]2[C:22](=[C:23]([C:29]#[N:30])[C:24]([F:28])=[CH:25][CH:26]=2)[CH2:21][CH2:20]1)[CH2:9][CH2:10][NH:11][CH2:12][C:13](OCC)=[O:14])=O)(C)(C)C.Cl>>[F:28][C:24]1[CH:25]=[CH:26][C:27]2[CH:19]([CH2:18][N:8]3[CH2:9][CH2:10][NH:11][CH2:12][C:13]3=[O:14])[CH2:20][CH2:21][C:22]=2[C:23]=1[C:29]#[N:30]

Participants

3

Reactant 2

HCID 313Hydrochloric AcidHCID 89526110Ethyl N-(2-{(tert-butoxycarbonyl)[(4-cyano-5-fluoro-2,3-dihydro-1H-inden-1-yl)methyl]amino}ethyl)glycinate

Product 1

HCID 895262715-Fluoro-1-[(2-oxopiperazin-1-yl)methyl]-2,3-dihydro-1H-indene-4-carbonitrile

Conditions

Temperature
140 °C

Procedure

To a flask charged with Ethyl N-(2-{(tert-butoxycarbonyl)[(4-cyano-5-fluoro-2,3-dihydro-1H-inden-1-yl)methyl]amino}ethyl)glycinate (30 mg, 0.072 mmol) was treated with HCl (1.78 ml, 7.2 mmol) to removed the BOC group. The solvent was removed when the deprotection was done. The residue was dissolved in EtOH (10 ml). To this solution was added a few drops of Hunig base. The solution was sealed in a microwave tube and heated to 140° C. for 30 minutes. The resulting title product was purified by MPLC. LC-MS (IE, m/z): 274 [M+1]+.

Workup

  1. customto removed the BOC group
  2. customThe solvent was removed when the deprotection
  3. dissolutionThe residue was dissolved in EtOH (10 ml)
  4. additionTo this solution was added a few drops of Hunig base
  5. customThe solution was sealed in a microwave tube
  6. customThe resulting title product was purified by MPLC

Sources & evidence

ORD record
ord-fc561904aed048f98ee19b33445bc032
Source dataset
uspto-grants-2015_04
Patent number
US08999990B2

Reaction notes

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