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

HRID 729414Notes

Reaction equation

HRID 729414 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-39cf450177104491ad666e42bacf3290
Source dataset
uspto-grants-2009_09
Patent number
US07582627B2

Reaction notes

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