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4-(Trifluoromethoxy)benzylamine → 2-[(4-Trifluoromethoxy-benzylamino)-methyl]-thiazole-4-carboxylic acid [2-(3-chloro-phenyl)-ethyl]-amide hydrochloride

HRID 1009203
Notes
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Reaction equation

HRID 1009203 reaction equation
Cl.[Cl:2][C:3]1[CH:4]=[C:5]([CH2:9][CH2:10][NH:11][C:12]([C:14]2[N:15]=[C:16]([CH2:19][NH2:20])[S:17][CH:18]=2)=[O:13])[CH:6]=[CH:7][CH:8]=1.[F:21][C:22]([F:33])([F:32])[O:23][C:24]1[CH:31]=[CH:30][C:27]([CH2:28]N)=[CH:26][CH:25]=1.C([BH3-])#N.[Na+]>C(O)(=O)C.C(O)C>[ClH:2].[Cl:2][C:3]1[CH:4]=[C:5]([CH2:9][CH2:10][NH:11][C:12]([C:14]2[N:15]=[C:16]([CH2:19][NH:20][CH2:28][C:27]3[CH:30]=[CH:31][C:24]([O:23][C:22]([F:21])([F:32])[F:33])=[CH:25][CH:26]=3)[S:17][CH:18]=2)=[O:13])[CH:6]=[CH:7][CH:8]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 5718464-(Trifluoromethoxy)benzylamineHCID 5003444Sodium cyanoborohydrideHCID 673043282-Aminomethyl-thiazole-4-carboxylic acid [2-(3-chlorophenyl)ethyl]amide hydrochloride

Product 1

HCID 673043512-[(4-Trifluoromethoxy-benzylamino)-methyl]-thiazole-4-carboxylic acid [2-(3-chloro-phenyl)-ethyl]-amide hydrochloride

Reagents, catalysts & solvents 2

HCID 176
Acetic Acid
Catalyst
HCID 702EthanolSolvent

Procedure

2-Aminomethyl-thiazole-4-carboxylic acid [2-(3-chlorophenyl)ethyl]amide hydrochloride (0.10 g, 0.3 mmol) and 4-(trifluoromethoxy)benzyl amine (0.06 g, 0.3 mmol) were mixed with sodium cyanoborohydride (1 M in THF, 0.6 mL), ethanol (5 mL), and a catalytic amount of acetic acid (2 drops). The mixture was heated at reflux for 24 hours. The mixture was concentrated in vacuo, diluted with water and extracted with methylene chloride. The combined organic layers were washed with sodium carbonate and brine, dried over sodium sulfate, filtered, and concentrated in vacuo. The crude amine was purified by flash chromatography (EtOAc/hexane), treated with HCl in dioxane, and concentrated in vacuo to afford the title compound: 1H NMR (400 MHz, d6-DMSO): 9.83 (br s, 2H), 8.43 (t, 1H), 8.32 (s, 1H), 7.66 (d, 2H), 7.44 (d, 2H), 7.25 (m, 4H), 4.58 (s, 2H), 4.37 (s, 2H), 3.53 (m, 2H), 2.86 (t, 2H); MS (ESI-LCMS) for C21H20ClF3N3O2S: 470 (MH+).

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 24 hours
  3. concentrationThe mixture was concentrated in vacuo
  4. additiondiluted with water
  5. extractionextracted with methylene chloride
  6. washThe combined organic layers were washed with sodium carbonate and brine
  7. dry with materialdried over sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. customThe crude amine was purified by flash chromatography (EtOAc/hexane)
  11. additiontreated with HCl in dioxane
  12. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-e0fed782977a4e8181fa16522db0bb7c
Source dataset
uspto-grants-2011_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07973061B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes