Trifluoroacetic acid → (3S,4R)-N3-(6-(2,6-dichloro-3,5-dimethoxyphenyl)quinazolin-2-yl)tetrahydrofuran-3,4-diamine

HRID 56369Notes

Reaction equation

HRID 56369 reaction equation
[Cl:1][C:2]1[C:7]([O:8][CH3:9])=[CH:6][C:5]([O:10][CH3:11])=[C:4]([Cl:12])[C:3]=1[C:13]1[CH:14]=[C:15]2[C:20](=[CH:21][CH:22]=1)[N:19]=[C:18]([NH:23][C@@H:24]1[CH2:28][O:27][CH2:26][C@@H:25]1[NH:29]C(=O)OC(C)(C)C)[N:17]=[CH:16]2.C(O)(C(F)(F)F)=O>C(Cl)Cl>[Cl:12][C:4]1[C:5]([O:10][CH3:11])=[CH:6][C:7]([O:8][CH3:9])=[C:2]([Cl:1])[C:3]=1[C:13]1[CH:14]=[C:15]2[C:20](=[CH:21][CH:22]=1)[N:19]=[C:18]([NH:23][C@H:24]1[C@@H:25]([NH2:29])[CH2:26][O:27][CH2:28]1)[N:17]=[CH:16]2

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 118043440tert-butyl ((3R,4S)-4-((6-(2,6-dichloro-3,5-dimethoxyphenyl)quinazolin-2-yl)amino)tetrahydrofuran-3-yl)carbamate

Product 1

HCID 118036616(3S,4R)-N3-(6-(2,6-dichloro-3,5-dimethoxyphenyl)quinazolin-2-yl)tetrahydrofuran-3,4-diamine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of tert-butyl ((3R,4S)-4-((6-(2,6-dichloro-3,5-dimethoxyphenyl)quinazolin-2-yl)amino)tetrahydrofuran-3-yl)carbamate (1.097 g, 2.049 mmol) in DCM (15 mL, 0.137 M) and TFA (11.7 g, 102 mmol) was stirred about 40 minutes at room temperature. The excess solvents were removed under reduced pressure. The yellow oil was dissolved into DCM (˜60 mL) and washed with aqueous 1N NaOH (˜30 mL). The aqueous layer was then diluted with brine (˜15 mL) and extracted with fresh DCM (3×30 mL). The combined organic layers were dried over sodium sulfate, filtered, concentrated down, and dried to yield (3S,4R)—N3-(6-(2,6-dichloro-3,5-dimethoxyphenyl)quinazolin-2-yl)tetrahydrofuran-3,4-diamine as a very light yellow foam (0.879 g, 99%).

Workup

  1. customThe excess solvents were removed under reduced pressure
  2. dissolutionThe yellow oil was dissolved into DCM (˜60 mL)
  3. washwashed with aqueous 1N NaOH (˜30 mL)
  4. additionThe aqueous layer was then diluted with brine (˜15 mL)
  5. extractionextracted with fresh DCM (3×30 mL)
  6. dry with materialThe combined organic layers were dried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated down
  9. customdried

Sources & evidence

ORD record
ord-2722b5df6bb84f8587e99d7185304d8a
Source dataset
uspto-grants-2016_09
Patent number
US09434700B2

Reaction notes

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