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2-Pyridinemethanamine → 1-(5-(5-Phenyl-4-((pyridin-2-ylmethyl)amino)phthalazin-1-yl)pyridin-3-yl)ethane-1,2-diol

HRID 593712
Notes
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Reaction equation

HRID 593712 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][C:10]=2[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:5]([C:18]2[CH:19]=[N:20][CH:21]=[C:22]([CH:24]3[CH2:28][O:27]C(C)(C)[O:25]3)[CH:23]=2)=[N:4][N:3]=1.[N:31]1[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=1[CH2:37][NH2:38]>C1(C)C=CC=CC=1.C(Cl)Cl>[C:12]1([C:10]2[CH:9]=[CH:8][CH:7]=[C:6]3[C:11]=2[C:2]([NH:38][CH2:37][C:32]2[CH:33]=[CH:34][CH:35]=[CH:36][N:31]=2)=[N:3][N:4]=[C:5]3[C:18]2[CH:23]=[C:22]([CH:24]([OH:25])[CH2:28][OH:27])[CH:21]=[N:20][CH:19]=2)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 195092-PyridinemethanamineHCID 904245884-Chloro-1-(5-(2,2-dimethyl-1,3-dioxolan-4-yl)pyridin-3-yl)-5-phenylphthalazine

Product 1

HCID 862702951-(5-(5-Phenyl-4-((pyridin-2-ylmethyl)amino)phthalazin-1-yl)pyridin-3-yl)ethane-1,2-diolYield 5.11%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolvent
HCID 6344
Dichloromethane
Solvent

Conditions

Temperature
100 °C

Procedure

To a solution of 4-chloro-1-(5-(2,2-dimethyl-1,3-dioxolan-4-yl)pyridin-3-yl)-5-phenylphthalazine (1.00 g, 2.39 mmol) in toluene (5 mL) was added pyridin-2-ylmethanamine (5.00 mL, 48.5 mmol) the contents were heated at 100° C. for 12 h. The reaction mixture was diluted with DCM (200 mL) and washed with 1.5N HCl (2 ×20 mL). The organic extract was dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure. The resulting crude was purified by preparative HPLC (Condition 18 as described in general methods) to obtain 1-(5-(5-phenyl-4-((pyridin-2-ylmethyl)amino)phthalazin-1-yl)pyridin-3-yl)ethane-1,2-diol (55.0 mg, 5.11%) as a white solid. The racemic product (50 mg) was resolved into individual enantiomers by chiral SFC (Condition 29 as described in general methods).

Workup

  1. washwashed with 1.5N HCl (2 ×20 mL)
  2. extractionThe organic extract
  3. dry with materialwas dried over anhydrous Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe resulting crude was purified by preparative HPLC (Condition 18 as described in general methods)

Sources & evidence

ORD record
ord-8bff044100bd440986ae462af654f76a
Source dataset
uspto-grants-2016_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09242966B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes