Trifluoroacetic acid → (4-Aminomethyl-benzyl)-(1H-benzimidazol-2-ylmethyl)(5,6,7,8-tetrahydro-quinolin-7-yl)-amine

HRID 2308292Notes

Reaction equation

HRID 2308292 reaction equation
C(OC([N:8]1[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=2[N:10]=[C:9]1[CH2:17][N:18]([CH2:29][C:30]1[CH:35]=[CH:34][C:33]([CH2:36][NH:37]C(OC(C)(C)C)=O)=[CH:32][CH:31]=1)[CH:19]1[CH2:28][C:27]2[N:26]=[CH:25][CH:24]=[CH:23][C:22]=2[CH2:21][CH2:20]1)=O)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH2:37][CH2:36][C:33]1[CH:32]=[CH:31][C:30]([CH2:29][N:18]([CH2:17][C:9]2[NH:8][C:12]3[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=3[N:10]=2)[CH:19]2[CH2:28][C:27]3[N:26]=[CH:25][CH:24]=[CH:23][C:22]=3[CH2:21][CH2:20]2)=[CH:35][CH:34]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 689014482-{[[4-(tert-Butoxycarbonylamino-methyl)-benzyl]-(5,6,7,8-tetrahydro-quinolin-7-yl)-amino]-methyl}-benzimidazole-1-carboxylic acid tert-butyl ester

Product 1

HCID 22601338(4-Aminomethyl-benzyl)-(1H-benzimidazol-2-ylmethyl)(5,6,7,8-tetrahydro-quinolin-7-yl)-amineYield 89.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 2-{[[4-(tert-Butoxycarbonylamino-methyl)-benzyl]-(5,6,7,8-tetrahydro-quinolin-7-yl)-amino]-methyl}-benzimidazole-1-carboxylic acid tert-butyl ester (120 mg, 0.20 mmol) in anhydrous CH2Cl2 (1 mL) was added TFA (1 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 (2:2:96 CH3OH—NH3 H2O—CH2Cl2) afforded the title compound (71 mg, 89%) 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 (2:2:96 CH3OH—NH3 H2O—CH2Cl2)

Sources & evidence

ORD record
ord-e50f6acbd442478cbda60d90e282664c
Source dataset
uspto-grants-2004_12
Patent number
US06835731B2

Reaction notes

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