HCID 57619253, compound → HCID 57619339, compound

HRID 1952163Notes

Reaction equation

HRID 1952163 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-dcdeaeea2ae741c4874560e37a38e9cb
Source dataset
uspto-grants-2013_03
Patent number
US08404700B2

Reaction notes

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