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Tert-butoxycarbonylalanine → (S)-1-(7-Bromo-6-methoxy-1-phenyl-1H-benzoimidazol-2-yl)ethylamine dihydrochloride

HRID 243076
Notes
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Reaction equation

HRID 243076 reaction equation
[Br:1][C:2]1[C:7]([O:8][CH3:9])=[CH:6][CH:5]=[C:4]([NH2:10])[C:3]=1[NH:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.[CH3:18][C@H:19]([NH:23]C(OC(C)(C)C)=O)[C:20](O)=O.C1C=NC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.[ClH:52]>C(Cl)Cl.O>[ClH:52].[ClH:52].[Br:1][C:2]1[C:3]2[N:11]([C:12]3[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=3)[C:18]([C@@H:19]([NH2:23])[CH3:20])=[N:10][C:4]=2[CH:5]=[CH:6][C:7]=1[O:8][CH3:9]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 85082Tert-butoxycarbonylalanineHCID 181649HOAtHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 681572213-Bromo-4-methoxy-N2-phenylbenzene-1,2-diamine

Product 1

HCID 68157275(S)-1-(7-Bromo-6-methoxy-1-phenyl-1H-benzoimidazol-2-yl)ethylamine dihydrochlorideYield 181.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 3-bromo-4-methoxy-N2-phenylbenzene-1,2-diamine (421 mg, 1.8 mmol), Boc-ala-OH (343 mg, 1.8 mmol) and HOAT (247 mg, 1.8 mmol) in DCM (10 mL) at 0° C. was added N-(3-dimethylaminopropyl)-n′-ethylcarbodiimide hydrochloride (383 mg, 1.99 mmol) and the reaction mixture stirred at 0° C. for 1 h. The reaction mixture was diluted with water and extracted with DCM (3×10 mL). The combined organic fractions were washed with brine, dried (MgSO4) and concentrated in vacuo. The residue was dissolved in HCl in dioxane (10 mL, 4 M) and the reaction mixture heated at 75° C. for 1 h. The reaction mixture was concentrated in vacuo to give the title product as a dark purple solid (758 mg, 100%). LCMS (Method C): RT=2.15 min, [M+H]+=346 & 348.

Workup

  1. extractionextracted with DCM (3×10 mL)
  2. washThe combined organic fractions were washed with brine
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated in vacuo
  5. dissolutionThe residue was dissolved in HCl in dioxane (10 mL, 4 M)
  6. temperaturethe reaction mixture heated at 75° C. for 1 h
  7. concentrationThe reaction mixture was concentrated in vacuo

Sources & evidence

ORD record
ord-f93c1d0bba7442a8958db92a736e1329
Source dataset
uspto-grants-2014_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08653089B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes