Acetonitrile → n-[4-(2,4-Dioxo(1,3-dihydroquinazolin-3-yl))phenyl]{[(5-chloro-3-fluoro(2-thienyl))sulfonyl]amino}carboxamide

HRID 1828160Notes

Reaction equation

HRID 1828160 reaction equation
[C:1]([NH:5][S:6]([C:9]1[S:10][C:11]([Cl:15])=[CH:12][C:13]=1[F:14])(=[O:8])=[O:7])(C)(C)C.C1CCN2C(=NCCC2)CC1.FC(F)(F)C(O)=[O:30].[NH2:34][C:35]1[CH:40]=[CH:39][C:38]([N:41]2[C:50](=[O:51])[C:49]3[C:44](=[CH:45][CH:46]=[CH:47][CH:48]=3)[NH:43][C:42]2=[O:52])=[CH:37][CH:36]=1.C(#N)C>C(O)(C(F)(F)F)=O>[O:52]=[C:42]1[N:41]([C:38]2[CH:39]=[CH:40][C:35]([NH:34][C:1]([NH:5][S:6]([C:9]3[S:10][C:11]([Cl:15])=[CH:12][C:13]=3[F:14])(=[O:8])=[O:7])=[O:30])=[CH:36][CH:37]=2)[C:50](=[O:51])[C:49]2[C:44](=[CH:45][CH:46]=[CH:47][CH:48]=2)[NH:43]1

Participants

6

Reactant 4

HCID 6342AcetonitrileHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 220643913-(4-Aminophenyl)-1,3-dihydroquinazoline-2,4-dione trifluoroacetateHCID 22064462(Tert-butyl)[(5-chloro-3-fluoro(2-thienyl))sulfonyl]amine

Product 1

HCID 22064426n-[4-(2,4-Dioxo(1,3-dihydroquinazolin-3-yl))phenyl]{[(5-chloro-3-fluoro(2-thienyl))sulfonyl]amino}carboxamideYield 34%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A 19 mg-sample (0.07 mmol) of (tert-butyl)[(5-chloro-3-fluoro(2-thienyl))sulfonyl]amine was dissolved in neat TFA and stirred for 1 h, concentrated in vacuo and used directly in the next transformation. This sample was dissolved in 150 uL of DCM and 21 mg (0.084 mmol) of DSC was added followed by 21 μL (0.14 mmol) of DBU. This solution was stirred for 18 h, 26 mg (0.07) of 3-(4-aminophenyl)-1,3-dihydroquinazoline-2,4-dione trifluoroacetate salt was added plus 150 μL of dry acetonitrile and refluxed for 2 h. This material was then purified on RP-HPLC to afford 11 mg (34%) of the desired product. ES-MS: M+H+=495 (Cl).

Workup

  1. concentrationconcentrated in vacuo
  2. dissolutionThis sample was dissolved in 150 uL of DCM
  3. addition21 mg (0.084 mmol) of DSC was added
  4. stirringThis solution was stirred for 18 h
  5. temperaturerefluxed for 2 h
  6. customThis material was then purified on RP-HPLC

Sources & evidence

ORD record
ord-e1309f7ba8864fac8ddeb1e67e604109
Source dataset
uspto-grants-2006_06
Patent number
US07056926B2

Reaction notes

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