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

HRID 970920
Notes
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Reaction equation

HRID 970920 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
ParticipantsProcedureWorkupSources & evidenceReaction notes

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-421cb7a5f02a45b7b0a4c00ef427a6e9
Source dataset
uspto-grants-2007_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07312234B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes