tert-Butyl (4-aminophenyl)carbamate → {4-[4-(2-Chloro-phenyl)-5-oxo-4,5-dihydro-3,4,7,9,9b-pentaaza-cyclopenta[a]naphthalen-8-ylamino]-phenyl}-carbamic acid tert-butyl ester

HRID 2370624Notes

Reaction equation

HRID 2370624 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[C:17](=[O:18])[C:16]2[C:11](=[N:12][C:13](S(C)=O)=[N:14][CH:15]=2)[N:10]2[CH:22]=[CH:23][N:24]=[C:9]12.[NH2:25][C:26]1[CH:31]=[CH:30][C:29]([NH:32][C:33](=[O:39])[O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[CH:28][CH:27]=1>C(OCC)(=O)C>[C:35]([O:34][C:33](=[O:39])[NH:32][C:29]1[CH:28]=[CH:27][C:26]([NH:25][C:13]2[N:12]=[C:11]3[C:16]([C:17](=[O:18])[N:8]([C:3]4[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=4[Cl:1])[C:9]4[N:10]3[CH:22]=[CH:23][N:24]=4)=[CH:15][N:14]=2)=[CH:31][CH:30]=1)([CH3:38])([CH3:36])[CH3:37]

Participants

4

Reactant 2

HCID 688611tert-Butyl (4-aminophenyl)carbamateHCID 681947574-(2-Chloro-phenyl)-8-methanesulfinyl-4H-3,4,7,9,9b-pentaaza-cyclopenta[a]naphthalen-5-one

Product 1

HCID 68194660{4-[4-(2-Chloro-phenyl)-5-oxo-4,5-dihydro-3,4,7,9,9b-pentaaza-cyclopenta[a]naphthalen-8-ylamino]-phenyl}-carbamic acid tert-butyl ester

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of Example 1E (330.0 mg, 0.917 mmol) and tert-butyl 4-aminophenylcarbamate (306 mg, 1.468 mmol) was heated in a capped vial at 100° C. for 1 hour. The residue was dissolved in ethyl acetate and washed with saturated aqueous NaHCO3. The organic layer was dried over MgSO4, filtered, concentrated, and purified on a 40 g column using the ISCO Companion flash system eluting with hexane/ethyl acetate (5:5 to 4:6) to provide the title compound.

Workup

  1. washwashed with saturated aqueous NaHCO3
  2. dry with materialThe organic layer was dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. custompurified on a 40 g column
  6. washeluting with hexane/ethyl acetate (5:5 to 4:6)

Sources & evidence

ORD record
ord-525c9851b57e483d834f5f41e4ad2f6b
Source dataset
uspto-grants-2014_04
Patent number
US08710065B2

Reaction notes

Loading…