[1-(3-Benzyloxy-1-cyclopropyl-6-fluoro-2,4-dioxo-1,2,3,4-tetrahydro-quinazolin-7-yl)-pyrrolidin-3-yl]-carbamic acid tert-butyl ester → 7-(3-Amino-pyrrolidin-1-yl)-1-cyclopropyl-6-fluoro-3-hydroxy-1H-quinazoline-2,4-dione

HRID 2270292Notes

Reaction equation

HRID 2270292 reaction equation
C(OC(=O)[NH:7][CH:8]1[CH2:12][CH2:11][N:10]([C:13]2[CH:22]=[C:21]3[C:16]([C:17](=[O:35])[N:18]([O:27]CC4C=CC=CC=4)[C:19](=[O:26])[N:20]3[CH:23]3[CH2:25][CH2:24]3)=[CH:15][C:14]=2[F:36])[CH2:9]1)(C)(C)C.FC(F)(F)C([O-])=O.FC(F)(F)C([O-])=O.FC(F)(F)C([O-])=O.[B+3]>FC(F)(F)C(O)=O>[NH2:7][CH:8]1[CH2:12][CH2:11][N:10]([C:13]2[CH:22]=[C:21]3[C:16]([C:17](=[O:35])[N:18]([OH:27])[C:19](=[O:26])[N:20]3[CH:23]3[CH2:24][CH2:25]3)=[CH:15][C:14]=2[F:36])[CH2:9]1

Participants

4

Reactant 2

HCID 56989620[1-(3-Benzyloxy-1-cyclopropyl-6-fluoro-2,4-dioxo-1,2,3,4-tetrahydro-quinazolin-7-yl)-pyrrolidin-3-yl]-carbamic acid tert-butyl esterHCID 178525683HCID 178525683, compound

Product 1

HCID 226330377-(3-Amino-pyrrolidin-1-yl)-1-cyclopropyl-6-fluoro-3-hydroxy-1H-quinazoline-2,4-dioneYield 106.4%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent2×

Procedure

A solution of [1-(3-benzyloxy-1-cyclopropyl-6-fluoro-2,4-dioxo-1,2,3,4-tetrahydro-quinazolin-7-yl)pyrrolidin-3-yl]-carbamic acid tert-butyl ester (Example G-3, 0.10 g, 0.22 mmol) in trifluoroacetic acid (TFA, 3.0 mL) was reacted with a 1.0 M solution of boron tris(trifluoroacetate) (1.1 mL, 1.1 mmol) in TFA and allowed to stir for 3 hours. The mixture was then concentrated and the residue rediluted in methanol and concentrated. This process was repeated two times. The residue was then triturated from diethyl ether and filtered to provide 0.075 g of the title compound as a solid, mp 244-245° C. (dec.).

Workup

  1. concentrationThe mixture was then concentrated
  2. additionthe residue rediluted in methanol
  3. concentrationconcentrated
  4. customThe residue was then triturated from diethyl ether
  5. filtrationfiltered

Sources & evidence

ORD record
ord-e57e8e93d95c4574ad1fafa01796be58
Source dataset
uspto-grants-2001_12
Patent number
US06331538B1

Reaction notes

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