HCID 57619253, compound → HCID 57619339, compound

HRID 1024306Notes

Reaction equation

HRID 1024306 reaction equation
[NH:1]1[C:5]2=[N:6][CH:7]=[CH:8][CH:9]=[C:4]2[C:3]([C:10]([C:12]2[CH:13]=[CH:14][C:15]([NH:18][CH2:19][C:20]3[CH:25]=[CH:24][C:23]([C:26]([F:29])([F:28])[F:27])=[CH:22][CH:21]=3)=[N:16][CH:17]=2)=[CH2:11])=[CH:2]1>O1CCCC1.CO>[NH:1]1[C:5]2=[N:6][CH:7]=[CH:8][CH:9]=[C:4]2[C:3]([CH:10]([C:12]2[CH:13]=[CH:14][C:15]([NH:18][CH2:19][C:20]3[CH:21]=[CH:22][C:23]([C:26]([F:27])([F:29])[F:28])=[CH:24][CH:25]=3)=[N:16][CH:17]=2)[CH3:11])=[CH:2]1

Participants

4

Reactant 1

HCID 57619253HCID 57619253, compound

Product 1

HCID 57619339HCID 57619339, compoundYield 5%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

5-[1-(1H-Pyrrolo[2,3-b]pyridin-3-yl)-vinyl]-pyridin-2-yl-(4-trifluoromethyl-benzyl)-amine (623, 0.043 g, 0.00011 mol) was dissolved in tetrahydrofuran (10 mL) and methanol (10 mL). The reaction was shaken under an atmosphere of hydrogen (30 psi) overnight. The reaction was filtered through Celite and the filtrate adsorbed onto silica and purified by silica gel column chromatography (ethyl acetate:hexanes) to provide the desired compound as a white solid (P-0388, 2.1 mg, 5%), consistent with compound structure by 1H-NMR and MS (ESI): [M+H+]+=397.6.

Workup

  1. filtrationThe reaction was filtered through Celite
  2. custompurified by silica gel column chromatography (ethyl acetate:hexanes)

Sources & evidence

ORD record
ord-526918335c92463693b09d335c104316
Source dataset
uspto-grants-2014_05
Patent number
US08722702B2

Reaction notes

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