Triethylamine → 3-Amino-7-[(S)-3-(tert-butoxycarbonylamino)pyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-1H-quinazoline-2,4-dione

HRID 10328Notes

Reaction equation

HRID 10328 reaction equation
[NH2:1][N:2]1[C:11](=[O:12])[C:10]2[C:5](=[CH:6][C:7](F)=[C:8]([F:13])[CH:9]=2)[N:4]([CH:15]2[CH2:17][CH2:16]2)[C:3]1=[O:18].C(N(CC)CC)C.[C:26]([O:30][C:31](=[O:38])[NH:32][C@H:33]1[CH2:37][CH2:36][NH:35][CH2:34]1)([CH3:29])([CH3:28])[CH3:27]>C(#N)C>[NH2:1][N:2]1[C:11](=[O:12])[C:10]2[C:5](=[CH:6][C:7]([N:35]3[CH2:36][CH2:37][C@H:33]([NH:32][C:31]([O:30][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:38])[CH2:34]3)=[C:8]([F:13])[CH:9]=2)[N:4]([CH:15]2[CH2:17][CH2:16]2)[C:3]1=[O:18]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 1514396(3S)-(-)-3-(tert-Butoxycarbonylamino)pyrrolidineHCID 114821773-Amino-1-cyclopropyl-6,7-difluoro-1H-quinazoline-2,4-dione

Product 1

HCID 586819023-Amino-7-[(S)-3-(tert-butoxycarbonylamino)pyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-1H-quinazoline-2,4-dioneYield 88.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 3-amino-1-cyclopropyl-6,7-difluoro-1H-quinazoline-2,4-dione (Example 24a) (50.0 mg, 0.20 mmol) and triethylamine (74 mg, 0.74 mmol) in acetonitrile (3 mL) is added (S)-pyrrolidin-3-yl carbamic acid tert-butyl ester (74 mg, 0.40 mmol). The solution is refluxed for 18 hours, the solvent is removed under reduced pressure, and the residue triturated with water. The solid is collected by filtration and air dried to afford 74 mg of the title compound. MS CI: m/z 420 (MH+).

Workup

  1. temperatureThe solution is refluxed for 18 hours
  2. customthe solvent is removed under reduced pressure
  3. customthe residue triturated with water
  4. filtrationThe solid is collected by filtration and air
  5. customdried

Sources & evidence

ORD record
ord-73b7642ecef9423da7f5d61ee74ce612
Source dataset
uspto-grants-2006_08
Patent number
US07094780B1

Reaction notes

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