Trifluoroacetic acid → HCID 86724294, compound

HRID 594894Notes

Reaction equation

HRID 594894 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]([NH:10][C:11]2[CH:12]=[C:13]3[C:22]4([CH2:26][O:25][C:24]([NH:27]C(=O)OC(C)(C)C)=[N:23]4)[C:19]4([CH2:21][CH2:20]4)[CH2:18][O:17][C:14]3=[CH:15][CH:16]=2)=[O:9])=[N:6][CH:7]=1.FC(F)(F)C(O)=O>C(Cl)Cl>[NH2:27][C:24]1[O:25][CH2:26][C:22]2([C:13]3[C:14](=[CH:15][CH:16]=[C:11]([NH:10][C:8]([C:5]4[CH:4]=[CH:3][C:2]([F:1])=[CH:7][N:6]=4)=[O:9])[CH:12]=3)[O:17][CH2:18][C:19]32[CH2:20][CH2:21]3)[N:23]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86724251HCID 86724251, compound

Product 1

HCID 86724294HCID 86724294, compoundYield 41.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of tert-butyl (6′-{[(5-fluoropyridin-2-yl)carbonyl]amino}dispiro[cyclopropane-1,3′-chromene-4′,4″-[1,3]oxazol]-2″-yl)carbamate (135 mg, 0.288 mmol) and CH2Cl2 (5.4 mL) was added trifluoroacetic acid (1.30 mL, 17.0 mmol) at ambient temperature. After stirring for 2 hours at the same temperature, the mixture was concentrated at reduced pressure. The residue was partitioned between CHCl3 and saturated aqueous NaHCO3. The organic layer was washed with water, dried over Na2SO4 and filtered. The filtrate was concentrated at reduced pressure, and the residue was purified with column chromatography on silica gel (CHCl3-EtOH, a linear gradient of EtOH from 0 to 20%) to afford N-(2″-aminodispiro[cyclopropane-1,3′-chromene-4′,4″-[1,3]oxazol]-6′-yl)-5-fluoropyridine-2-carboxamide (43.6 mg).

Workup

  1. concentrationthe mixture was concentrated at reduced pressure
  2. customThe residue was partitioned between CHCl3 and saturated aqueous NaHCO3
  3. washThe organic layer was washed with water
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated at reduced pressure
  7. customthe residue was purified with column chromatography on silica gel (CHCl3-EtOH

Sources & evidence

ORD record
ord-c718b508cf0442be8796ed200147ecd8
Source dataset
uspto-grants-2016_01
Patent number
US09242973B2

Reaction notes

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