1,1'-Carbonyldiimidazole → HCID 59398274, compound

HRID 39823Notes

Reaction equation

HRID 39823 reaction equation
[C:1]([O:5][C:6]([N:8]([CH2:31][C:32]1[CH:41]=[CH:40][C:35]2[O:36][CH2:37][CH2:38][O:39][C:34]=2[CH:33]=1)[CH:9]1[CH2:14][CH2:13][N:12]([CH2:15][CH2:16][N:17]2[C:26]3[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=3)[C:20]([C:27](O)=[O:28])=[CH:19][C:18]2=[O:30])[CH2:11][CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(N1C=CN=C1)(N1C=CN=C1)=O.[CH3:54][S:55]([NH2:58])(=[O:57])=[O:56].N12CCCN=C1CCCCC2>O1CCCC1>[O:36]1[C:35]2[CH:40]=[CH:41][C:32]([CH2:31][N:8]([CH:9]3[CH2:14][CH2:13][N:12]([CH2:15][CH2:16][N:17]4[C:26]5[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=5)[C:20]([C:27]([NH:58][S:55]([CH3:54])(=[O:57])=[O:56])=[O:28])=[CH:19][C:18]4=[O:30])[CH2:11][CH2:10]3)[C:6](=[O:7])[O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[CH:33][C:34]=2[O:39][CH2:38][CH2:37]1

Participants

6

Reactant 4

HCID 682631,1'-CarbonyldiimidazoleHCID 72879MethanesulfonamideHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 59397872HCID 59397872, compound

Product 1

HCID 59398274HCID 59398274, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

To 5 mL of tetrahydrofuran suspension containing 0.10 g of 1-(2-(4-((tert-butoxycarbonyl)(2,3-dihydro-1,4-benzodioxin-6-ylmethyl)amino)piperidin-1-yl)ethyl)-2-oxo-1,2-dihydroquinoline-4-carboxylic acid, 58 mg of 1,1′-carbonyldiimidazole was added, and stirred at 50° C. for 1 hour. The reaction mixture was cooled to the room temperature, then 84 mg of methanesulfonamide and 0.13 mL of 1,8-diazabicylo[5.4.0] undec-7-ene were added, and stirred at room temperature for 2 hours. The solvent was removed under reduced pressure, water was added, and adjusted to pH 4 with 1 mol/L hydrochloric acid. The resulting solid was filtered to afford 0.10 g of tert-butyl (2,3-dihydro-1,4-benzodioxin-6-ylmethyl)(1-(2-(4-(((methylsulfonyl)amino)carbonyl)-2-oxoquinolin-1(2H)-yl)ethyl)piperidin-4-yl)carbamate as a white solid.

Workup

  1. additionwas added
  2. temperatureThe reaction mixture was cooled to the room temperature
  3. stirringstirred at room temperature for 2 hours
  4. customThe solvent was removed under reduced pressure, water
  5. additionwas added
  6. filtrationThe resulting solid was filtered

Sources & evidence

ORD record
ord-4b67871e0d914212bbfebce1e2aa3952
Source dataset
uspto-grants-2013_09
Patent number
US08524738B2

Reaction notes

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