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Hydrochloric Acid → 6-(2-Methyl-6-(1,2,3,4-tetrahydroisoquinolin-1-yl)phenyl)-3-morpholinoquinolin-2-amine

HRID 1028953
Notes
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Reaction equation

HRID 1028953 reaction equation
[C:1]1([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([CH3:17])[C:12]=2[C:18]2[CH:19]=[C:20]3[C:25](=[CH:26][CH:27]=2)[N:24]=[C:23]([NH2:28])[C:22]([N:29]2[CH2:34][CH2:33][O:32][CH2:31][CH2:30]2)=[CH:21]3)[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][N:2]=1.[BH4-].[Na+].Cl>CO>[CH3:17][C:13]1[CH:14]=[CH:15][CH:16]=[C:11]([CH:1]2[C:10]3[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=3)[CH2:4][CH2:3][NH:2]2)[C:12]=1[C:18]1[CH:19]=[C:20]2[C:25](=[CH:26][CH:27]=1)[N:24]=[C:23]([NH2:28])[C:22]([N:29]1[CH2:34][CH2:33][O:32][CH2:31][CH2:30]1)=[CH:21]2
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 673247536-(2-(3,4-Dihydroisoquinolin-1-yl)-6-methylphenyl)-3-morpholinoquinolin-2-amine

Product 1

HCID 533286426-(2-Methyl-6-(1,2,3,4-tetrahydroisoquinolin-1-yl)phenyl)-3-morpholinoquinolin-2-amine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A suspension of 6-(2-(3,4-dihydroisoquinolin-1-yl)-6-methylphenyl)-3-morpholinoquinolin-2-amine (0.0075 g, 0.017 mmol) in MeOH (0.50 mL) was treated with NaBH4 (25.0 mg, 0.661 mmol) and stirred at ambient temperature overnight. On following day, reaction mixture treated with 2N HCl and stirred for 2 h. The mixture was filtered and the filtrate was purified directly by reverse phase HPLC (1-90% acetonitrile/H2O, TFA modifier, 20 min). Single fraction freeze-dried to afford 6-(2-methyl-6-(1,2,3,4-tetrahydroisoquinolin-1-yl)phenyl)-3-morpholinoquinolin-2-amine (2,2,2-trifluoroacetate salt). MS (ESI, pos. ion) m/z: 451 (M+1).

Workup

  1. waitOn following day
  2. customreaction mixture
  3. stirringstirred for 2 h
  4. filtrationThe mixture was filtered
  5. customthe filtrate was purified directly by reverse phase HPLC (1-90% acetonitrile/H2O, TFA modifier, 20 min)
  6. customSingle fraction freeze-dried

Sources & evidence

ORD record
ord-a4399b33448049b59e574decc32e704f
Source dataset
uspto-grants-2014_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08735384B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes