HCID 57619253, compound → HCID 57619339, compound

HRID 1367419Notes

Reaction equation

HRID 1367419 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-32d97c8cb84d45ca924fa6dbd25d157b
Source dataset
uspto-grants-2011_02
Patent number
US07893075B2

Reaction notes

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