Chloroform → HCID 478668, compound

HRID 1756583Notes

Reaction equation

HRID 1756583 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:16](=[CH:17][C:18]=1[N:19]1[CH2:24][CH2:23][N:22](C(OC(C)(C)C)=O)[CH:21]([CH3:32])[CH2:20]1)[N:15]1[C:6](=[N:7][C:8]3[C:13]([C:14]1=[O:33])=[CH:12][CH:11]=[CH:10][CH:9]=3)[C:5]2=[O:34].C(Cl)(Cl)Cl>C(Cl)Cl.FC(F)(F)C(O)=O>[F:1][C:2]1[CH:3]=[C:4]2[C:16](=[CH:17][C:18]=1[N:19]1[CH2:24][CH2:23][NH:22][CH:21]([CH3:32])[CH2:20]1)[N:15]1[C:6](=[N:7][C:8]3[C:13]([C:14]1=[O:33])=[CH:12][CH:11]=[CH:10][CH:9]=3)[C:5]2=[O:34]

Participants

5

Reactant 2

HCID 6212ChloroformHCID 478667HCID 478667, compound

Product 1

HCID 478668HCID 478668, compoundYield 75%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of 8-fluoro-9-(3-methyl-4-t-butyloxycarbonylpiperazinyl)-indolo[2,1-b]quinazoline-6-12-dione (0.19 g, 0.4 mmol) (from Example 53) in methylene chloride (7 mL) and trifluoroacetic acid (7 mL) was stirred for 1 h. Chloroform was added and the chloroform/methylene chloride solution was washed with saturated sodium bicarbonate. The organic layer was separated, dried and concentrated to give a solid. Purification of the crude product by silica gel chromatography (chloroform eluent) gave the title compound in 75% yield: mp 225°-227° C.; 1H NMR (300 MHz, CDCl3) δ 8.40 (d, 1H), 8.18 (d, 1H), 8.03 (d, 1H), 7.85 (t, 1H), 7.65 (t, 1H) 7.50 (d, 1H), 4.3 (m, 1H), 3.86-3.76 (m, 2H), 3.13-3.04 (m, 4H), 2.8 (t, 1H) 1.75 (s, 3H).

Workup

  1. washthe chloroform/methylene chloride solution was washed with saturated sodium bicarbonate
  2. customThe organic layer was separated
  3. customdried
  4. concentrationconcentrated
  5. customto give a solid
  6. customPurification of the crude product by silica gel chromatography (chloroform eluent)

Sources & evidence

ORD record
ord-dd05a6917a324e0495d6bb20a9b05f04
Source dataset
uspto-grants-1995_08
Patent number
US05441955

Reaction notes

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