HCID 86633811, compound → HCID 57857127, compound

HRID 1643319Notes

Reaction equation

HRID 1643319 reaction equation
[N+:1]([C:4]1[CH:31]=[CH:30][C:7]([C:8]([NH:10][C:11]2[CH:16]=[C:15]([C:17]3[S:18][CH:19]=[CH:20][CH:21]=3)[CH:14]=[CH:13][C:12]=2[NH:22][C:23](=[O:29])[O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:9])=[CH:6][CH:5]=1)([O-])=O.[H][H]>[Pd].CCOC(C)=O.C1COCC1>[NH2:1][C:4]1[CH:31]=[CH:30][C:7]([C:8]([NH:10][C:11]2[CH:16]=[C:15]([C:17]3[S:18][CH:19]=[CH:20][CH:21]=3)[CH:14]=[CH:13][C:12]=2[NH:22][C:23](=[O:29])[O:24][C:25]([CH3:28])([CH3:26])[CH3:27])=[O:9])=[CH:6][CH:5]=1

Participants

5

Reactant 2

HCID 86633811HCID 86633811, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 57857127HCID 57857127, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21939870Tetrahydrofuran ethyl acetateSolvent

Procedure

To a solution of tert-butyl [2-[(4-nitrobenzoyl)amino]-4-(2-thienyl)phenyl]carbamate (598 mg, 1.36 mmol) in 1:1 EtOAc/THF was added 10 mol % Pd/C (136 mg, 1.36 mmol). The reaction mixture was evacuated and refilled with hydrogen (2×). The black reaction mixture was stirred in a parr shaker under 50 psi of hydrogen overnight. The mixture was filtered through a pad of celite (with EtOAc then CH2Cl2 washes) and concentrated to provide tert-butyl [2-[(4-aminobenzoyl)amino]-4-(2-thienyl)phenyl]carbamate which was confirmed by MS: cal'd 410.1 (MH+), exp 410.1 (MH+).

Workup

  1. customThe reaction mixture was evacuated
  2. additionrefilled with hydrogen (2×)
  3. customThe black reaction mixture
  4. filtrationThe mixture was filtered through a pad of celite (with EtOAc
  5. concentrationCH2Cl2 washes) and concentrated

Sources & evidence

ORD record
ord-93d0efae9b4f45f9b547c02ad0fa499b
Source dataset
uspto-grants-2012_02
Patent number
US08119685B2

Reaction notes

Loading…