Trifluoroacetic acid → HCID 22601492, compound

HRID 2308293Notes

Reaction equation

HRID 2308293 reaction equation
C(OC(=O)[NH:7][CH2:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][N:16]([S:27]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=2[N+:36]([O-:38])=[O:37])(=[O:29])=[O:28])[CH:17]2[CH2:26][C:25]3[N:24]=[CH:23][CH:22]=[CH:21][C:20]=3[CH2:19][CH2:18]2)=[CH:11][CH:10]=1)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH2:7][CH2:8][C:9]1[CH:10]=[CH:11][C:12]([CH2:15][N:16]([CH:17]2[CH2:26][C:25]3[N:24]=[CH:23][CH:22]=[CH:21][C:20]=3[CH2:19][CH2:18]2)[S:27]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=2[N+:36]([O-:38])=[O:37])(=[O:28])=[O:29])=[CH:13][CH:14]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 68897591HCID 68897591, compound

Product 1

HCID 22601492HCID 22601492, compoundYield 57.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of (4-{[(2-Nitro-benzenesulfonyl)-(5,6,7,8-tetrahydro-quinolin-7-yl)-amino]-methyl}-benzyl)-carbamic acid tert-butyl ester (160 mg, 0.29 mmol) in anhydrous CH2Cl2 (2 mL) was added TFA (2 mL). The resultant solution was stirred at room temperature overnight. The mixture was concentrated in vacuo, dissolved with MeOH, and added NaHCO3. The mixture was stirred for 20 min, diluted with CH2Cl2, filtered through celite. The crude product was purified by flash chromatography on silica gel (1:1:98 CH3OH—NH3 H2O—CH2Cl2) afforded the title compound (75 mg, 57%) as a white foam.

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. dissolutiondissolved with MeOH
  3. additionadded NaHCO3
  4. additiondiluted with CH2Cl2
  5. filtrationfiltered through celite
  6. customThe crude product was purified by flash chromatography on silica gel (1:1:98 CH3OH—NH3 H2O—CH2Cl2)

Sources & evidence

ORD record
ord-19ed364bef574891977af5ca76134084
Source dataset
uspto-grants-2004_12
Patent number
US06835731B2

Reaction notes

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